Blog Article 

 Preparing for Success Supplement 

Michael Santos

Michael Santos

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  • Rishi’s journey highlights the importance of seizing opportunities, proactive learning, and early action. From his early business ventures as a child to his later endeavors, Rishi’s story illustrates the significance of making effective use of time and resources. Our students should recognize how we can all rebuild our lives through continuous learning and taking bold steps to create positive change.


  • Our students should learn ideals related to a growth-oriented mindset, an ability to identify opportunities, and the principles of gratitude and humility. Rishi also outlines several critical business lessons, including concepts like valuation and venture capital-related terms. Additional lessons involve the need to develop basic skills in math, communication, and critical thinking.

Lesson Requirements:

  • Watch the video that accompanies the lesson
  • Write a definition of each word highlighted in bold and written in italics
  • Use ten of the vocabulary words in a sentence
  • Respond to a minimum of three open-ended questions by following instructions at the end of the lesson.

Lesson Outcome:

  • Participants will increase their vocabulary by at least ten words.
  • Participants will improve writing skills and their ability to contemplate how their responses to open-ended questions relate to their prospects for success upon release.
  • Participants will add to their journal, demonstrating a self-directed, self-improvement pathway to prepare for success upon release.

Our team at Prison Professors routinely reaches out to the most successful members of society to impart sound life lessons to our students. This lesson plan focuses on Rishi, an inspiring individual who achieved remarkable feats based on his insatiable curiosity and relentless pursuit of opportunities.

From his narrative, we explore several success principles that propelled Rishi to prosperity, including an optimistic attitude, tireless work ethic, and eagerness to give back to his community. As he recounts his career journey, he also shares insightful business tips that can spur aspiring entrepreneurs to establish lucrative businesses. By emulating leaders like Rishi, all of us can increase our likelihood of rebuilding our lives as we seek to earn our freedom.


Born in Chicago, Rishi’s life was deeply shaped by the values of his immigrant parents. Coming from India in pursuit of career opportunities, they instilled in him the importance of hard work and the drive to seize opportunities, principles that parallel our coursework modules.

The ideal of hard work is evident as Rishi recounts his father’s journey from modest beginnings to becoming a physician in the United States. His father overcame hardships through his dedication to his academic studies, excelling in high school exams that enabled him to secure a scholarship to finish college and medical school in India. Later, drawn by the demand for medical professionals in the U.S., he relocated stateside despite immense challenges.

With only $14 upon arrival and facing bias due to his nationality, his dad persevered, advancing his education at the University of Illinois through a fellowship and building a successful medical practice. Leading by example, Rishi’s father illustrated for his young son that a can-do attitude and a tireless work ethic would lead him to prevail against adversities.

Rishi cherished his parents’ wisdom, leading him to cultivate a deep appreciation for the opportunities he enjoyed as a young man. Often, he visited his father’s hometown in India, which illustrated the stark contrast between his father’s early life and Rishi’s childhood experience. His sense of gratitude—something we should all strive for—drove him to always aim to give back to his community.

Based on his parents’ lessons, he fostered an “immigrant mentality,” which drove him to develop an entrepreneurial spirit. When he was around 10 years old, an art peddler came to his childhood home to attempt to sell paintings. Intrigued by the idea of earning a profit through door-to-door sales, he followed the vendor’s example. Realizing his sister had a watercolor kit, he teamed up with his sibling to paint and sell pictures to neighbors before his mother shuttered the operation.

Though he now calls this initial attempt to start a business “silly one-day” affair, this early experience shows us that Rishi was always a “doer.” He never allowed the fear of rejection to stop him from striving for his goals. Rather, he looked at failures as learning experiences, remaining mindful of opportunities to deliver value to others. Even today, he believes the fundamentals to his success in business are the same as when he was a child: A business owner must meet and exceed their customer’s needs. By doing so, the businessperson can continue to sell and potentially grow their customer base through word-of-mouth. Based on this principle, we should ask ourselves: What opportunities do I have to contribute to others? How can I meet and exceed someone else’s needs and expectations? And what skills can help me along the way?

Rishi’s innate curiosity continued to open doors for him as he grew older. In the late 1990s—when he was about 12—personal computers started coming into widespread use. Rishi became the de facto technical expert for computers in his household and among neighbors, given the general public’s inexperience with the then-nascent technology.

Recognizing his knack for computers, Rishi started a consulting business to teach others digital literacy. Initially, he employed fellow students, but as demand grew, he expanded to hiring from a local community college. Always eager to help others, Rishi collaborated with a neighborhood retirement home to establish a computer lab for the residents. This endeavor allowed the elderly to communicate with their families digitally, a particularly rewarding experience for Rishi. His consultancy grew to unprecedented levels. Eventually, he partnered with CompUSA—a large nationwide retailer—to handle some of his business operations, given the high levels of demand.

Even in the midst of tragedy, Rishi sought to identify opportunities and give back to his community. The dreadful events of 9/11 profoundly impacted his generation, leading many students, including him, to delve deeper into global issues. He approached Newsweek magazine with a unique proposal: A sponsorship that would involve supplying magazines to students, facilitating discussions, and potentially organizing conferences on global subjects. He convinced the magazine to accept his proposal through a compelling pitch: Providing the students with periodicals would come at little cost to the organization and increase the company’s circulation. Based on this example, we should all ask ourselves: What opportunities are there for me to deliver value to others?


Stories like Rishi’s should inspire all our students to overcome personal challenges and begin working toward fulfilling their dreams. As I served nearly three decades in prison, I consistently sought role models like Rishi to identify the success principles that empowered their achievements. I realized that by following their examples, I could reach my aspirations and triumph despite my past.

One lesson we learned is about overcoming a fear of rejection. Before he was even ten years old, he found the courage to persuade neighbors to buy paintings in his first business adventure. Armed with youthful confidence and a simple idea, he didn’t dread hearing ‘no.’ Rather, his ambition drove him to pursue more ventures, including a digital consultancy at only 12. With his tenacious spirit, he made a positive impact on his community, helping elderly people connect with loved ones. Even amid a calamity like the 9/11 attacks, he gave back to others, collaborating with Newsweek magazine to help fellow students understand world events at a time of deep societal trauma and confusion.

Let’s follow his example and seek opportunities to help others. We must recognize that while Rishi identified opportunities that led to his prosperity, his early ventures still benefited other people. Symbiotic relationships—those built on mutual gains by all involved—can open doors to positive interactions and community support for all our listeners.

Mentorship can offer our students a chance to build such a symbiotic relationship. Consider how Rishi was always willing to listen and learn from others. His dad was a seminal influence, imparting invaluable lessons about resilience that fueled Rishi’s future achievements. Rishi benefited from his father’s wisdom while, in turn, his father now benefits from his legacy: a highly successful child with undying gratitude for his parents. Not everyone has the advantage of a father figure as they grow up. However, everyone can begin looking for positive role models, community support groups, and professional networks. Following Rishi’s example, we can find mentors willing to help us and, in turn, contribute to society as we seek to rebuild our lives.

We also learn the value of humility and gratitude, which are both apparent as Rishi emphasizes his deep respect for his parents’ sacrifices. His father never became deterred by his challenges as an immigrant. His dad faced unfamiliar surroundings and a hostile job market, an experience that may resonate with our students. Yet despite these odds, his father was grateful for the opportunities to begin anew, remembering that an action-oriented mindset and a solid work ethic would lead him to prevail. His sacrifices paid off: through his persistence, he became successful, enabling his son to enjoy a more privileged upbringing than he had.

By achieving our dreams, we too can attain prosperity for ourselves and generations to follow. The message for our students is clear: We must maintain a purpose-driven outlook to overcome our challenges. We can never make excuses.

  • Considering Rishi’s upbringing shaped by his immigrant parents, how have your own experiences shaped your values and outlook on life?
  • Who were some unexpected role models you encountered along your journey, and what positive lessons did you learn from them?
  • How can you apply Rishi’s lesson on overcoming a fear of rejection to face possible rejections or biases you might face?
  • Given Rishi’s emphasis on giving back, how can you use your unique skills or experiences to contribute positively to your community?
  • In what ways can you practice gratitude and humility in your daily life, despite the challenges you might encounter?

Rishi’s Entrepreneurial Journey:

After starting college, Rishi became more determined than ever to venture into entrepreneurship. Initially, Rishi aimed to embark on traditional avenues like medicine and law, yet a chance encounter with a professor altered his mindset. Beforehand, Rishi believed that launching a startup required years of prior experience. However, the professor presented a compelling counterargument: young people, who are likely unburdened by extensive familial and financial commitments, are often in the best position to start a business.

Bolstered by this revelation, Rishi left college to set up different companies. His initial attempts met with failure, but rather than discourage him, these experiences motivated him to improve his skills in persuasive communication and further his education. Later, he teamed up with likeminded individuals, and together they crafted a business plan that won in a competition. This early victory emboldened Rishi, paving the way for his later professional feats.

Rishi’s business idea centered on making available transformative technology to improve patient learning in medical settings. Now present in a quarter of all doctor’s offices and hospitals in the United States, Rishi’s company produces tools that inform patients in the waiting room about new products and services, including health foods, treatment options, and medical devices. Patients would then be ready to discuss or consider these products during their consultations with physicians.

A eureka moment led Rishi to build this business. He stumbled across this idea when he read an article about informational screens broadcasting information on products to customers at big box stores like Walmart and Best Buy. As a child, he proposed a similar concept for his father’s clinic. To alleviate waiting times, Rishi suggested his father record educational sessions on conditions like diabetes so patients could learn about their illness ahead of their appointments. He realized that the same concept could benefit companies that wanted to promote their health-related products directly to patients before they see their doctors.

His business boomed, leading him to acquire a substantial fortune and contribute to his community. He invested in other entrepreneurs, often being their first source of capital. He also provided them with advice, mentorship, and support on key business aspects like hiring, sales, and product development. To date, he has invested in over 70 companies, including startups, private equity companies, and venture capital funds, contributing to the creation of thousands of jobs and billions of dollars in economic impact.

Rishi’s Business Insights:

As Rishi describes his business experience, he shared critical insights of interest to all our students, especially aspiring entrepreneurs. Many of our listeners may face challenges in securing employment in the traditional job market. By learning from successful business leaders like Rishi, we can potentially develop independent income streams that can accelerate our quests to build law-abiding lives and meaningful careers.

One of the most important lessons from Rishi’s relates to developing a business plan. We can think of this plan like a roadmap for a business. Entrepreneurs like Rishi use it to document what their business is, what they want to achieve, and how they plan to accomplish those goals. As illustrated in the table below, the business plans should feature key concepts.

Reflecting on the food establishment mentioned in our conversation, let’s consider a pizza stand for our business plan.

Problem Statement:  Definition: Pointing out a need or challenge that a business will address. As Rishi notes, this should identify whether the business is addressing a pressing need (painkiller) or providing an enhancement (vitamin).Example: In dense urban areas, residents often seek fresh, authentic pizza but have few local options.
Solution  Definition: The way a business plans to meet that need or challenge.Example: A mobile pizza oven stand, which prepares and serves authentic, freshly baked pizzas in busy city spots.
Commercialization Strategy:  Definition: The method a business uses to sell its products or services and earn money.Example: Stationing the mobile pizza oven in bustling squares during peak mealtimes and promoting daily specials on social media.
Operational Scale Plan:  Definition: Ideas for making the business bigger over time.Example: Starting with one mobile pizza stand and later expanding to have multiple stands across various city locations.
Financials:  Definition: Details about the money: starting costs, predicted earnings, and expenses.Example: Determining the cost to produce a single pizza, setting its selling price, and calculating the number needed to be sold to cover costs and gain profit.

Understanding Valuation:

Rishi then teaches us about “valuation,” which is figuring out how much a business is worth. Consider the pizza stand. To know its value, the owner of the pizza stand would look at other similar pizza businesses in their area. Rishi stresses that when a business is just an idea (like a “napkin idea,” a term for a thought jotted down on a napkin), it’s worth less than when it’s an operational business.

To better understand valuation, consider a scenario where an old car is being sold. The car’s condition, the demand in the market, its brand, and other factors play into determining its price. In a similar vein, determining a business’s value involves evaluating its performance, the market’s demand for its services or products, its future potential, and other factors.

Venture Capital and Valuation:

We also learn about “venture capital,” which is when an investor gives money to help a business grow. While discussing venture capital, Rishi explains the difference between “pre-money” and “post-money” valuations. Imagine the pizza stand is worth $300 before acquiring money from an investor. If they give $100, the value of the stand becomes $400. If the pizza stand does well, its value could become much more, like $1,000. This growth is beneficial for both the business owner and the investor.

To better understand venture capital, let’s consider a scenario in which an investor gives money to the owner of our pizza stand. Venture capital generally involves six stages: the initial pitch, screening, due diligence, investment, post-investment, and an exit strategy. We describe how each stage relates to the pizza stand in the table following the infographic.

Initial pitch  Definition: The stage where entrepreneurs present their business idea to potential investors.Example: The pizzeria owner has a concept for a unique mobile pizza oven stand targeting busy city locations, showcasing the market potential, differentiation factors, and initial financial forecasts.
Screening  Definition: The process where venture capitalists review and filter the received pitches, selecting the ones that align with their interests and investment criteria.Example: The venture capital firm reviews various pitches and identifies the mobile pizza stand idea as innovative and potentially profitable, matching their focus on food and retail startups.
Due Diligence  Definition: A rigorous investigation phase where the venture capitalist validates the claims made during the pitch, evaluating the business’s viability.Example: The venture capital firm assesses the entrepreneur’s market research, verifies the demand in urban areas, and cross-checks the financial projections for the pizza stand.
Investment  Definition: The stage where the venture capitalist decides to invest capital into the startup in exchange for equity or another form of return.Example: Convinced of its potential, the venture capital firm agrees to invest $200,000 in the mobile pizza stand for a 20% equity stake, helping the business kickstart its operations
Post-investment  Definition: After the investment, this phase involves monitoring, mentoring, and sometimes guiding the startup to ensure its growth and success.Example: With the investment, the pizza stand is operational in three city spots. The venture capital firm assists with networking, provides marketing advice, and holds quarterly review meetings to track progress.
Exit Strategy  Definition: The plan for venture capitalists to sell their stake in the business, aiming to realize a return on their investment.Example: As the pizza brand gains city-wide recognition, a large food chain expresses interest in acquiring it. The venture capital firm sells its 20% stake for $2 million, achieving a 10x return on their initial investment.

Multiples for Value:

Rishi also discusses “multiples” which are ways to find a business’s value based on how much money it makes. He gives the example of Domino’s Pizza being worth 10 times its earnings. If someone has a startup, they might say it’s worth five times its expected earnings because it has a lot of potential. Rishi learned that comparing to big companies can help startups know how much they might be worth.

Free Cash Flow Matters:

Rishi stresses that businesses are valued based on their potential to generate free cash flow, a primary metric in the stock market. Free cash flow signifies the very essence of why businesses operate: to earn money. To gauge the value of a business, one can draw parallels with similar publicly traded companies. For instance, someone intending to start a pizzeria might look at publicly traded entities like Domino’s or Papa John’s to discern their worth and understand the multiples at which they trade. The value of established brands like Domino’s isn’t just tied to their current earnings but also factors in their brand longevity, recognition, and scale. For a budding entrepreneur, this provides a rough benchmark for valuation.

Two other investment tips stand out from Rishi’s journey:

  • Find investors who believe in the vision: Rishi says it’s best to get money from investors who are excited about a business idea. They need to care about what the business wants to achieve.
  • Start small and grow: Rishi advises starting with just one unit of a business and getting money for that first. Once that succeeds, it becomes easier to get more money to expand.

From Rishi’s story, we should recognize that success in the entrepreneurial world is a blend of past experiences, continuous learning, and understanding market dynamics. His insight into starting a business can help us transform our past experiences into future opportunities.


A crucial takeaway is Rishi’s open-mindedness and willingness to learn from others. Like his father years before, Rishi’s professor played a pivotal mentorship role in his life. By exposing the young man to the lucrative potential of entrepreneurship, the professor helped Rishi find the confidence to define his version of success: operating a profitable independent business. Once Rishi identified his long-term goal, he worked tirelessly, eventually attaining unprecedented levels of wealth. His hard work also benefited others: he improved patient learning in medical settings and provided livelihoods to countless others.

His story embodies the idea that proactive learning goes beyond just formal education. We should follow in his footsteps and adopt a relentless drive to continuously grow, adapt, and evolve. All our audience members can start on this pathway through self-directed reading and outreach to professionals in a career field of interest.

Another message stands out from Rishi’s story: We must seize opportunities at the earliest available moment. As he describes the “eureka moment” that led him to develop his business idea, we can infer that Rishi did not waste time when putting his idea into action. Rather, he was proactive, preparing an award-winning business proposal and working with likeminded individuals to ensure its success. The lesson is clear for our students: We must progress toward our goals every day. Success demands consistency and self-discipline. We encourage our students to pursue constructive routines-those that help us develop basic skills to ensure our success-as they seek to rebuild their lives.

Any self-directed education routine should incorporate activities that promote development in three fundamental areas: math, communication, and critical thinking. As illustrated in the table below, Rishi had to become proficient in each area to succeed in business. Likewise, our students must grasp these concepts to thrive upon reentry.

Skill area:Explanations:
Math Skills:  From the story: Rishi’s journey into entrepreneurship required a firm grasp of financial calculations, from business valuations to understanding investment dynamics and using multiples to gauge his venture’s worth.How it relates to us: Understanding financial concepts can offer our students a sense of control over their financial future. Such skills can guide informed decision-making, promote financial stability, and form the basis for entrepreneurial ventures.
Communication Skills:  From the story: Rishi’s story showcases the power of persuasion and storytelling, from pitching his business plan or his business vision in a compelling and engaging way.How it relates to us: Enhancing communication skills can empower our students to advocate for themselves effectively. Skills like persuasive argumentation can be invaluable during job interviews or trying to find housing. Storytelling can turn past experiences into powerful narratives of resilience and growth.
Critical Thinking Skills:  From the story: Rishi demonstrated adaptability and problem-solving abilities by pivoting after initial failure. He demonstrated strategic thinking in his alignment with suitable investors and his understanding of market dynamics. He also exhibited an ability to integrate past experiences with new knowledge, forming a unique business proposition.How it relates to us: These skills, which involve problem-solving, adaptability, and strategic planning, can help our audience members navigate life’s challenges and opportunities. The ability to synthesize experiences can turn past lessons into steppingstones for growth and learning.
  • Does Rishi’s story persuade you to become an entrepreneur? Why or why not?
  • How do you believe Rishi refined his communication, critical thinking, and math skills as he progressed in his role as a business leader?
  • How does Rishi’s story mirror our lessons about seeking positive, like-minded people?
  • How can the concept of valuation—determining the worth of something—help you both in business and in personal contexts?
  • Why is continuous learning important for personal and professional development in any field?


Rishi should stand out to all of us as a champion. From his days as a child brimming with questions about the world to his remarkable entrepreneurial feats, Rishi story is one of curiosity and ambition. His desire to continuously learn paved the way for him to blossom into a highly influential entrepreneur and provide livelihoods to countless others. He never lost his childlike sense of wonder; his curiosity drove him to revolutionize patient care and support our country through billions in tax dollars.

As he recounted his journey, we learned about the success principles that led him to thrive: a zest for proactive learning and seizing opportunities along with an unwavering commitment to improvement. His father instilled those values in him, teaching his son that resilience and a can-do spirit can lead anyone to prevail over adversities. While not everyone enjoys having the support of a parental figure growing up, Rishi’s story shows us that it’s never too late to reach out to mentors and find role models to emulate.

Rishi, like all successful people, embodies each of the concepts that we encourage our students to adapt in the ten modules of our coursework:

Values: We must define success.From a young age, Rishi knew he wanted to delve into entrepreneurship and business. His story begins with a clear understanding of what success looked like to him.
Goals: We must set clear goals that align with our definition of success.Rishi identified opportunities, such as when he collaborated with CompUSA. His goals were in alignment with his vision, whether it was selling electronics or partnering with a major retailer. His goals were also SMART: Specific, measurable, action oriented, realistic and time bound.
Attitude: We must make a commitment with the right attitude.Rishi was not only committed to his ventures for monetary reasons but because he genuinely wanted to solve problems. His commitment was unwavering and based on a solid foundation of genuine interest and passion.
Aspiration: We must see ourselves as being something more than the challenges we currently face.Even during college, Rishi didn’t see his youth as a limitation. When presented with the idea that he could start a business then and there, he embraced it wholeheartedly. He always aspired for more, such as entering the venture capital space.
Action: We must take incremental action steps.He wasn’t just a dreamer; he was a doer. Whether it was selling his sister’s paintings or understanding the potential in a business opportunity, Rishi took tangible actions towards his goals.
Accountability: We must hold ourselves accountable.Rishi made detailed plans and strategies, exemplifying his sense of responsibility. He had been cultivating business ideas for years and held himself accountable to bring them to fruition.
Awareness: We must stay aware of opportunities.Since childhood, Rishi had an eye out for opportunities, from selling paintings to recognizing a gap in the electronics market. His keen sense of awareness set the stage for his entrepreneurial pursuits.
Authenticity: We must be authentic.Rishi’s endeavors came from a genuine place of passion and interest. His success wasn’t rehearsed; it was a natural progression due to his authentic approach to business.
Achievement: We must celebrate small victories.Every step in Rishi’s journey, from his first sale to major business deals, was a testament to the importance of acknowledging and celebrating milestones.
Appreciation: We must show appreciation for the blessings that come our way.Rishi’s dedication to sharing his story with our students and contributing to educational endeavors showcases his gratitude for his journey and the opportunities that shaped it. He valued giving back and sharing the wisdom he gained.

Mass incarceration remains a blot on our society, an injustice that demands our collective action. Every story of success and innovation reminds us of the potential trapped behind bars—potential that could be shaping our future. As we admire and learn from trailblazers like Rishi, let’s also commit to rebuilding our lives, ensuring that we can rebuild our lives and make our mark on the world.

To encourage your learning, this lesson plan includes supplemental documents: 

  • Glossary
  • Appendix A: Related Reading and Resources
  • Appendix B: Supporting Organizations
  • Appendix C: Potential Careers

All our students can become successful like Rishi. Attaining his level of achievement requires dedication, continuous learning, and a willingness to adapt to ever-changing circumstances.

Critical Thinking Questions:

Choose any of three questions below. Write a response for each of the three questions you choose. In your response, please write at least three paragraphs, with a minimum of three sentences each.

This exercise in personal development will help you develop better critical-thinking skills, and better writing skills. There are no right or wrong answers to these questions. We’re striving to learn how to think differently, and how to communicate more efficiently. Try to use some of the vocabulary words from this lesson in your responses.

  1. How can building symbiotic relationships help you as you seek to rebuild your life, establish a career, and develop professional networks?
  2. What daily situations have you experienced that could be turned into opportunities to help others?
  3. How can you resonate with Rishi’s father’s ability to transform adversities into advantages?
  4. Have you developed solutions for overlooked needs or gaps in your own surroundings?
  5. Who, like Rishi’s professor, has provided unexpected guidance or inspiration in your journey?
  6. Which of Rishi’s business strategies or insights appeals most to you?
  7. How would you ensure you stay ahead in a field or interest area you’re passionate about?
  8. How does Rishi’s story illustrate that proficiency in math, critical thinking, and communication are vital in any vocation?
  9. What does your version of success look like in 5, 10, or 20 years?
  10. Other than those listed, in what ways do you believe Rishi reflects the principles in our ten coursework modules?


  • Alleviate (verb) – to make a situation or a pain less severe.
  • Alter (verb) – to change or modify.
  • Bias (noun) – prejudice in favor of or against one thing, person, or group.
  • Bolster (verb) – to support or strengthen.
  • Calamity (noun) – an event causing sudden damage or distress; a disaster.
  • Collaborate (verb) – to work jointly on an activity or project.
  • Consultancy (noun) – a professional practice that gives expert advice within a particular field.
  • Cultivate (verb) – to prepare and use land for crops; to develop a skill or quality.
  • De facto (adjective/adverb) – in fact, whether by right or not.
  • Delve (verb) – to investigate or research deeply and thoroughly.
  • Deterred (verb, past tense) – discouraged from doing something.
  • Digital Literacy (noun) – the ability to use information and communication technologies to find, evaluate, create, and communicate information.
  • Dreadful (adjective) – extremely bad or unpleasant.
  • Eager (adjective) – wanting to do or have something very much.
  • Embody (verb) – to represent in physical form.
  • Embolden (verb) – to give someone the courage or confidence to do something.
  • Empower (verb) – to give someone the authority or power to do something.
  • Endeavor (noun/verb) – a serious attempt or effort / to try hard.
  • Eureka Moment (noun) – a sudden realization or discovery.
  • Feat (noun) – an achievement that requires great courage, skill, or strength.
  • Foster (verb) – to encourage or promote the development of.
  • Free Cash Flow (noun) – the cash a company generates after cash outflows to support operations and maintain its capital assets.
  • Fundamental (noun) – a central or primary rule or principle.
  • Gauge (noun/verb) – an instrument for measuring / to assess.
  • Hostile (adjective) – unfriendly; antagonistic.
  • Ideal (noun) – a person or thing regarded as perfect or a standard of perfection.
  • Immense (adjective) – extremely large or great.
  • Infer (verb) – to deduce or conclude from evidence and reasoning.
  • Intrigue (noun/verb) – a secret plot / to arouse the curiosity or interest of.
  • Insatiable (adjective) – having an appetite or desire that is impossible to satisfy.
  • Knack (noun) – a skill or ability.
  • Literacy (noun) – the ability to read and write.
  • Lucrative (adjective) – producing a great deal of profit.
  • Metric (noun) – a standard of measurement.
  • Multiple (noun, in business) – the number of times a particular amount is to be multiplied with something, especially the price-earnings ratio of a company’s shares.
  • Nascent (adjective) – just beginning to exist or develop.
  • Parallel (verb) – to be similar or analogous to.
  • Peddler (noun) – a person who sells goods, especially in the street.
  • Periodical (noun) – a magazine or newspaper published at regular intervals.
  • Pitch (noun/verb) – a tone’s perceived frequency / to throw or set up.
  • Post-money Valuation (noun) – the value of a company immediately after an investment has been made.
  • Pre-money Valuation (noun) – the valuation of a company prior to an investment or financing.
  • Private Equity (noun) – capital that is not listed on a public exchange.
  • Pivotal (adjective) – of crucial importance relating to the success of something.
  • Quest (noun) – a search or pursuit to find or obtain something.
  • Relentless (adjective) – oppressively constant; incessant.
  • Resonate (verb) – to produce or be filled with a deep, reverberating sound or to evoke emotions.
  • Seminal (adjective) – strongly influencing later developments.
  • Shutter (noun/verb) – a device that opens and closes to expose the film in a camera / to close.
  • Sibling (noun) – a brother or sister.
  • Startup (noun) – a newly established business.
  • Stateside (adverb/adjective) – in or to the US / relating to the US.
  • Stark (adjective) – severe or bare in appearance or outline.
  • Symbiotic (adjective) – involving interaction between two different organisms living in close physical association.
  • Tenacious (adjective) – tending to keep a firm hold of something.
  • Trauma (noun) – a deeply distressing or disturbing experience.
  • Undying (adjective) – never ending or fading.
  • Valuation (noun) – the estimation of the worth of something.
  • Vendor (noun) – a person or company offering something for sale.
  • Venture Capital (noun) – capital invested in a project where there is substantial risk.
  • Word-of-mouth (noun) – information passed by verbal communication.

This appendix provides a curated list of books based on insights we gleaned from Rishi’s interview. These insights can help our students learn more about the nuances of entrepreneurship and the stock market.

Insight on valuations: Y Combinator—Safe Financing Documents

General Reading
“The Lean Startup” by Eric Ries – This book offers practical guidance for launching a startup, emphasizing the importance of testing ideas quickly and efficiently, a concept aligned with Rishi’s proactive approach.   “The Art of Possibility” by Rosamund Stone Zander and Benjamin Zander – This book encourages a mindset shift that focuses on abundance, creativity, and embracing opportunities, which resonates with Rishi’s story of turning unexpected experiences into business ideas.   “Zero to One” by Peter Thiel – Thiel’s insights on building startups from scratch can inspire justice-impacted individuals to see unique opportunities where others might not and create innovative solutions.   “The $100 Startup” by Chris Guillebeau – This book provides practical advice on launching a business with minimal investment, aligning with Rishi’s emphasis on starting small and building from there.   “The Lean Entrepreneur” by Brant Cooper and Patrick Vlaskovits – This book provides a detailed framework for applying lean startup principles and customer-focused strategies to build successful businesses, a concept mirrored in Rishi’s journey.
Stock Market-Related Literature
“A Random Walk Down Wall Street” by Burton G. Malkiel – This classic book introduces the concept of efficient markets and provides insights into investing strategies, helping individuals understand how the stock market works.   “The Intelligent Investor” by Benjamin Graham – Graham’s timeless wisdom offers guidance on value investing and the importance of a long-term perspective, which can be especially relevant for justice-impacted individuals seeking financial stability.   “How to Make Money in Stocks” by William J. O’Neil – This book focuses on the principles of technical analysis and growth investing, providing practical strategies for identifying potential winners in the stock market.   “The Little Book of Common Sense Investing” by John C. Bogle – Bogle, the founder of Vanguard, emphasizes the benefits of low-cost index fund investing, a strategy that aligns with Rishi’s advice on understanding market dynamics.   “One Up On Wall Street” by Peter Lynch – Lynch’s approachable style introduces readers to the world of stock investing, emphasizing the value of researching companies and staying informed.   “Market Wizards” by Jack D. Schwager – This book offers insights from successful traders and investors, showcasing diverse strategies and perspectives that justice-impacted individuals can learn from.

Appendix B: Supporting Organizations

Several organizations can help our students seeking to find entrepreneurship. The organizations below provide services that can our listeners determine their career path and receive needed support and training.

Defy Ventures

Defy Ventures offers entrepreneurship and employment training, helping people start their own businesses or find meaningful employment upon reentry.


Email: [email protected]

Phone: (917) 720-1870

The Last Mile

The Last Mile provides technology training and coding education, preparing individuals for successful reintegration into the workforce, including opportunities in entrepreneurship and technology.


Email: [email protected]

Homeboy Industries

Homeboy Industries offers job training, education, and support services to individuals transitioning back to employment, including entrepreneurial opportunities and support.


Phone: (323) 526-1254

The Center for Employment Opportunities (CEO)

CEO provides comprehensive employment services, focusing on job placement, skill development, and career advancement.


Phone: (212) 422-4430

YouthBuild USA

YouthBuild offers education, job training, and leadership development to young adults, helping them build skills for success in entrepreneurship and other fields.


Phone: (617) 623-9900

The Prison Entrepreneurship Program (PEP)

PEP focuses on providing business education and mentorship, fostering entrepreneurship and personal development to create successful futures.


Phone: (346) 299-3952

Appendix C: Potential Careers

Based on Rishi’s story, we’ve identified several entrepreneurial paths that may open doors to the most industrious of our students. As society advances, new niches emerge, and with them, innovative business opportunities. Inspired by Rishi’s journey, here are various entrepreneurial roles that resonate with the themes of innovation, adaptability, and societal impact.

Healthcare Solutions Entrepreneur

Description: Identify gaps in the healthcare system, particularly in patient care and experience, and develop solutions to bridge those gaps, such as tools to streamline patient-provider communication.

Tech-Driven Social Impact Entrepreneur

Description: Use technology to create solutions for pressing societal challenges, aiming for both profit and positive societal change.

Local Business Innovator

Description: Introduce a novel product or service tailored to local needs, making use of understanding community needs, and delivering unique solutions.

Content Strategy Entrepreneur

Description: Design content platforms that serve niche markets, ensuring they have access to tailored content that resonates with their experiences.

Eco-friendly Products Entrepreneur

Description: Focus on creating sustainable, eco-friendly products or services that not only cater to a growing market but also contribute to environmental welfare.

Personal Branding Consultant

Description: Help individuals, especially professionals or public figures, in building and managing their personal brand, leveraging the power of digital platforms.

Custom Tech Solutions Provider

Description: Develop tailored technology solutions for specific industries or businesses, such as custom software for healthcare providers.

Community Engagement Specialist

Description: Facilitate and foster connections between businesses and the communities they serve, creating mutually beneficial relationships.

Educational Tools Innovator

Description: Create tools or platforms that enhance the educational experience, making it more accessible, interactive, and engaging.

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