Blog Article 

 Resilience and Rebuilding 

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Michael Santos

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Resilience and Rebuilding Careers after Prison:

Resilience and Rebuilding Careers after Prison


  • Now an affluent real estate investor, Bruce shares his touching life story, recounting his journey from an impoverished childhood background to becoming a self-made success story. Our interview explores how resilience, skill development, and strategic thinking led him to bounce back after setbacks and prosper in his current career. His path serves as an inspiration for our students and all who aspire to rise above their circumstances. In our interview, he details how strong relationship-building skills and a keen ability to identify opportunities were foundational to his success.


  • Our listeners should recognize the importance of a goal-oriented mindset, a willingness to work hard, and awareness of opportunities, which were all instrumental in Bruce’s story. Our students should also recognize how math, critical thinking, and communication skills propelled Bruce toward prosperity. Finally, our students should identify how business knowledge and collaboration led Bruce to grow his investment revenue substantially.

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 engages in dialogues with the highest-achieving members of society to identify the success principles that can transform the lives of our students. Bruce, now an affluent investor in the homestay industry, overcame poverty as a youth by learning from role models and identifying opportunities for a better future. Today, he enjoys a lucrative career and a fulfilling life with a loving wife and six children.

By following the example of leaders like Bruce, any of our audience members can begin their journey toward success. He imparts sound business advice that can help our students rebuild their lives and establish lawful revenue streams outside conventional employment.


Bruce grew up in a poverty-stricken environment in the inner city in the U.S. Midwest, raised by a single mother with four children. None of his siblings nor his mother had completed high school. Common among the inner-city dwellers was the misguided belief that “that money was evil, rich people were bad,” and no opportunities existed for individuals who lacked access to wealth. Initially, Bruce succumbed to the same self-limiting and defeatist beliefs, feeling trapped by the cycle of poverty. He likely internalized negative stereotypes based on his surroundings and concluded that upward economic mobility was unattainable.

Fortunately, his mindset shifted when he started questioning his circumstances, longing for a better future. An interaction with a man in his neighborhood who refurbished bicycles and built wishing wells sparked this transformation. This man taught Bruce that he could create value and earn profit from providing seemingly mundane tasks or services, so long as there was a market need. Contrary to the adage that a person “needs money to make money,” Bruce learned that attaining success requires having the right attitude and seeking opportunities. Bruce overcame the challenges of his upbringing by upholding a results-oriented mindset and robust work ethic, behaviors that any of our students can immediately begin emulating.  

The mentorship he received was a game-changer, influencing him to actively seek advice and guidance from more experienced individuals throughout his life. He emphasizes the importance of reaching out to successful businesspeople for advice, as they often enjoy discussing their successes and businesses. Following his example, we must seek to learn from others, especially those more experienced and knowledgeable than we are, to achieve our aspirations.

Despite his challenging upbringing, Bruce completed high school and enlisted in the Navy to further his education through the GI Bill. Within six months, he traveled to nine countries where he witnessed extreme destitution, an experience that broadened his worldview and deepened his appreciation for the opportunities available in the United States.

Upon returning from military service, Bruce attended a junior college, earning two associate degrees. Initially, he struggled to get admitted into a four-year college because of his poor high school grades. Acting upon the advice of a friend, he earned better marks while in junior college, enabling him to later transfer to a larger university of his choice. While pursuing his studies, he maintained a rigorous work ethic, balancing school with a full-time job. He also created an expansive support network by participating in fraternity chapters; some of his fraternity brothers have been influential in his later business success. His involvement in the social group also led Bruce to sharpen his communication and interpersonal skills, which have served him well throughout his career.  

Educational Opportunities for Justice-Impacted Individuals

Justice-impacted individuals, including veterans and retired Service members, have access to a variety of educational programs:

GI Bill: Justice-impacted veterans can avail of both Post-9/11 and Montgomery GI Bills, enabling them to access up to 48 months of education benefits if they paid into the Montgomery GI Bill program while serving.

Health Care for Re-entry Veterans (HCRV) Initiative: This program aids incarcerated veterans with planning for reintegration into the community after release, aiming to prevent homelessness and ensure a successful transition.

Veteran Justice Outreach (VJO) Program: The VJO program focuses on preventing unnecessary criminalization of mental health issues by facilitating veterans’ timely access to VA healthcare and other appropriate services when involved in the justice system.

Federal Pell Grants: Starting July 1, 2023, inmates enrolled in a sanctioned prison education program at federal or state correctional institutions could be eligible for Federal Pell Grants, expanding educational opportunities while incarcerated. Pell Grants do not require military service for eligibility,

After college, Bruce found a job in sales, where he rapidly climbed the corporate ladder, eventually supervising multiple locations and managing millions of dollars of inventory and approximately 55 employees. He attained a lucrative career at only 26 years old–a feat challenging even for professionals with more work experience and advantaged backgrounds. The job was demanding and provided him with opportunities for personal development, including valuable sales training. However, after the birth of his first child, Bruce decided to leave his corporate job to start his own business, given his desire for a better work-life balance and spend more time with his family.


Our team at Prison Professors shares life lessons from leaders like Bruce to improve the lives of justice-impacted people. We believe role models like Bruce illustrate success principles that empower professional and personal growth. As I served a 45-year sentence, I consistently sought to learn from individuals like Bruce–an exemplar in our society–to guide me as I strived to overcome the challenges of incarceration.

A crucial takeaway for our listeners is the value of mentorship. As Bruce progressed through his career, mentorship has consistently played a vital role in his growth and success. Seeking better outcomes for himself, Bruce built rapport with a neighbor who earned profits repairing bicycles and wishing wells. Let’s use the wishing well as a metaphor for everyone seeking to better themselves in our audience. When someone takes the time to repair the well, it symbolizes hope and fulfillment to passersby. Similarly, when a mentor invests time in someone–the student–can follow their mentor’s example and inspire positive change in others. By learning from the wisdom and experiences shared by mentors, we can use their knowledge to accelerate our attainment of success and avoid making unnecessary mistakes.

Like all successful people, Bruce thrived in his career based on his communication, math, and critical thinking proficiency. These skills are fundamental to the success of our audience members.

Communication skills   Bruce demonstrated an exceptional knack for sharing his story and inspiring others throughout our interview. By concisely and articulately recounting his journey, Bruce clearly explained his life challenges and steps to overcome them, giving us invaluable insight into the sacrifices needed for success. As an erudite speaker, Bruce can quickly build rapport and persuade others, essential skills that led him to thrive in several industries.   Likewise, we encourage our listeners to hone their verbal and written communication skills before release. Returning citizens must sharpen their ability to communicate to become more effective at building positive connections with potential employers and fostering supportive networks that aid in successful reintegration.
Math skills   Bruce also teaches us the value of solid math skills, emphasizing that mathematical proficiency is vital for financial success and business management. By understanding math, our listeners can learn to calculate profit and assess risk, avoiding costly business decisions and increasing their likelihood of making rather than losing money. He believes so strongly in the power of math that he is involved in a nonprofit organization that promotes financial literacy.  
Critical thinking skills   Critical thinking also played a pivotal role in Bruce’s journey. We can infer that he relied on sound reasoning to advance professionally, such as taking advantage of the GI Bill to further his education and creating strong support networks that served him throughout his career. He sought out mentors consistently in his journey, reflecting his ability to select positive influences in his personal network based on his discernment.   Similarly, we must cultivate our reasoning skills to assess information, make informed decisions, and solve problems effectively. With these skills, we stand a better chance of finding employment and housing, while enhancing our chances of successful reintegration.

Lastly, Bruce’s narrative highlights the need to remain aware of opportunities and actively pursue one’s goals. Despite the scarcity of financial resources in his early years, he didn’t allow these circumstances to dictate his future.

Our students can learn from this example by exploring “creative financing,” a term often used in real estate to describe unconventional means of buying land or property. For our students, creative financing can entail identifying potential investors who have the financial means but lack the time for direct involvement. Students can secure the capital necessary for their business ventures by crafting compelling narratives and consistently demonstrating their value.

  • How might your upbringing and experiences shape your beliefs and attitudes toward wealth creation and opportunities for advancement?
  • How can mentorship and guidance from experienced individuals positively impact your journey as you seek to rebuild your life?
  • How might participating in educational programs and initiatives contribute to your successful reintegration?
  • How can critical thinking skills help you navigate complex situations, make informed decisions, and plan for your future?
  • What available resources can you sharpen your financial literacy, and how can this skill help you?

Business Ventures:

After leaving his sales role, Bruce pursued new opportunities and a better work-life balance. His journey was a roller-coaster of varied business endeavors, each teaching him valuable lessons. Through his story, we delve into themes of resilience, the wisdom of learning from mistakes, the power of a positive attitude, and the importance of a never-quit work ethic.

Early Real Estate Experience

Bruce entered the real estate industry with some of his fraternity brothers, presumably in the early 2000s, specializing in buying and flipping properties. Most of their investments were financed by private investors who were interested in real estate but didn’t want to be directly involved in the legwork. Bruce and his colleagues negotiated creative financing deals with these investors to raise capital. However, the subprime market crash in 2008 and 2009 resulted in significant losses. This loss was a critical learning experience for Bruce, teaching him to adapt and revamp his business model.

Wealth Management Consultation:

Bruce then embarked on a venture with a clear objective: to improve wealth management for affluent clients. He noticed that various professionals offered advice independently, leading to a lack of coordination and potentially ineffective strategies. Recognizing this gap, he decided to address it directly. His goal wasn’t simply to add another opinion to the mix but to facilitate better communication and establish a more cohesive approach to wealth management.

In response, Bruce and his business partner created a process connecting all these professionals, ensuring their plans worked cohesively to manage the clients’ wealth. Bruce spent around five years in this business.

Financial Literacy Venture:

While providing services to the wealthy, Bruce recognized another market need: many small and less affluent business owners needed access to financial information readily available to the rich. This gap inspired Bruce to start a business in financial literacy, focused on helping small business owners and individuals with limited capital learn how to grow their wealth.

Bruce and his team simplified complex financial concepts and offered free educational seminars and workshops within various communities. Those interested in learning often became clients. He was involved in this venture for approximately 13 years until he experienced burnout, prompting him to seek more fulfilling opportunities.

Short-term Rentals/Hospitality Business:

In 2018, Bruce unexpectedly stumbled upon his next opportunity: the homestay industry. That year, he found an inaccurately advertised real estate opportunity online. The ad described the property as a single cabin with ten bedrooms, though it was a plot with five two-bedroom cabins. The previous owner had plans to convert the property into a vacation spot, piquing Bruce’s interest even though he lacked funds.

Bruce and his wife negotiated a unique deal with the property owner, proposing direct payments instead of relying on a bank loan. This strategy enabled them to repurpose the cabins into Airbnb-style rentals. Bruce found this short-term rental business model preferable to having long-term tenants.

Bruce and his wife saw potential. They believed they could make the business profitable by renovating the cabins and through effective marketing. They researched comparable businesses to ensure their investment was sound and analyzed all potential costs, such as cleaning services, utilities, and property taxes. The property, free of mortgages or debts, was priced at $380,000. The seller agreed to a two percent interest rate and a payment of $3,000 per month.

Bruce and his wife crafted a structured payment plan and made an offer to the owner that allowed them to reinvest revenue back into the property. They aimed to pay off the debt as quickly as possible, a goal based on thorough calculations and risk assessments. They also prepared for unexpected costs, like damage from natural disasters.

They engaged in several sound business practices, namely:

  • Their original plan was to pay off the loan in 10 years but are now aiming for a 5-year plan. Bruce sought to reduce risks and build equity by paying off the loan quickly.
  • Their plan included paying off the property and upgrading the cabins to increase their value. They believed the cabins were worth more than the asking price, providing a potential exit strategy.
  • He factored in external risks like market downturns or unforeseen events affecting revenue.
  • By balancing their rental rates with their monthly payments, they turned the business into a profitable venture with a safety net.

Today, the business is nearing its payoff and generating substantial revenue. Now Bruce and his wife are involved in additional opportunities, such as boat rentals and operating a country market with a bait shop, along with a music venue. It’s called The Dry Docks, where they host outdoor concerns to benefit their local food pantry. The couple also plays an active role in the local community, including nonprofit work, spotlighting their belief in community engagement as a vital part of running a successful business.

Bruce and his wife brought their business vision to life through unrelenting hard work and strategic improvements, achieving an 85 percent occupancy rate during the peak season. Their success stands as a strong validation of their business model.

To visualize the rapid rate of expansion of Bruce’s homestay business, a timeline is included in supplementary documents at the end of this lesson plan. The timeline details key moments in Bruce and his wife’s operations, highlighting significant events since 2018.


Bruce’s journey is a testament to how learning from failures and taking advantage of second chances can lead to remarkable transformations. He had experienced significant setbacks in his previous business ventures yet never gave up. Instead, he harnessed the lessons from his failures, using them as steppingstones in redefining his entrepreneurial journey. His resilience is a potent reminder that our past challenges and disappointments do not define our future potential. Instead, they provide valuable insights to guide our actions and decisions.

Our students may have doubts about their ability to recalibrate after facing adversity. The example of Bruce’s rebound from failure to success conveys a powerful message of hope and resilience. It emphasizes that a setback or failure is not the end of the road but rather an opportunity for a fresh start.

We also learn crucial lessons on business development with limited capital. Though Bruce lacked finances, he overcame this hurdle through strategic decision-making. First, he was keenly observant and recognized gaps in the market that he could address, such as poor wealth management coordination and financial literacy for small business owners. Second, he showed resilience, learning from each business venture and remaining positive despite setbacks.

Bruce and his wife also engaged in best practices as they began their involvement in the homestay industry that aspiring business owners should emulate, though these lessons may be applied in traditional employment roles. Among those lessons include:

  • Understanding financial basics and return on investment: Bruce and his wife needed to understand the basic financials associated with the business venture they were about to undertake. They had to determine the costs and the potential income. Their goal was to ensure the business was financially viable and could provide a return on their investment.
    • Takeaway: Our students should have a solid understanding of the financials of any business. With basic math skills, our students can determine if an investment is worthwhile and if they can expect a reasonable return.
  • Importance of due diligence: Bruce and his wife conducted thorough due diligence before entering their business deal. They spent time researching similar businesses, assessing the market, and getting to know the operational details, like how much they could charge for rent and the costs associated with the cabins.
    • Takeaway: Before committing to a business deal, we must research and understand the market and the business. Using critical thinking skills, our students can make informed decisions and potentially avoid costly mistakes.
  • Use of mathematical models for financial projections: Bruce and his wife developed a financial model to help them project income and expenses and determine whether they could afford the payment. With basic arithmetic, they used a simple division of the total cost by the number of cabins and then estimated the monthly rental income required per cabin to cover the costs and desired profit.
    • Takeaway: Learning how to create and use financial models is essential for business planning. Our students can use models to help them make projections about a business’s performance and make informed decisions.
  • Importance of negotiation: Bruce and his wife initially offered a ten-year financing deal to the owner, but then came back with a five-year plan. This shift shows that the initial proposal may not be the final agreement, and it’s crucial to be flexible and able to negotiate.
    • Takeaway: Our students must develop sound communication skills for negotiations, which can be highly beneficial in business. Being able to negotiate effectively can lead to more favorable agreements and potentially save money.
  • Long-term planning and exit strategy: In addition to the short-term financial calculations, Bruce and his wife also considered their long-term plans and exit strategy. They saw the potential to increase the value of the property over time, which would create additional wealth and provide an option to sell the cabins in the future.
    • Takeaway: We must always consider our long-term plans and exit strategy when starting a business. Understanding the end goal can help guide business decisions and strategies.

Bruce and his wife illuminate the critical importance of sound critical thinking, communication, and mathematical skills, which are vital to success in any industry. Following Bruce’s example, we can begin sharpening these skills ahead of our release to find lucrative career opportunities, even if we lack capital or face adversities. By honing these same skills, our students also increase their chances of success in a business venture or in conventional employment.

  • How can you apply Bruce’s experience of starting a business with minimal capital to your own entrepreneurial or career aspirations?
  • Reflecting on Bruce’s ability to bounce back from setbacks, how can you develop resilience in facing challenges?
  • How might you identify market needs in your community that could inspire business ventures or opportunities for personal growth?
  • Considering Bruce’s approach to risk assessment, how can you develop a strategic mindset to minimize risks and maximize your potential success?
  • What steps can you take to actively engage with your local community and contribute to its growth and development?


Bruce is a champion in our society whose story illustrates how our students can overcome challenges and earn their freedom. Despite his impoverished upbringing in a low-income, inner-city neighborhood, Bruce never let his circumstances define him. Instead, he chose to seize opportunities, cultivate an optimistic attitude, and pursue continuous learning, thereby exemplifying resilience and resourcefulness.

Key to his transformation was his ability to learn from mentors. As a young man, Bruce found a role model in his neighborhood, who kindled his entrepreneurial spirit. This mentor taught Bruce that anyone could attain a lawful, meaningful career even if they lacked capital. Rather, aspiring business owners must identify a market need and uphold a productive attitude and work ethic to thrive in a given vocation.

Bruce’s insight also mirrors our lessons on skill development. Throughout his professional trajectory, he relied on his critical thinking, communication, and mathematics to carve out a successful career in sales and later as an investor. He used these skills to identify gaps in the market and create businesses that fulfilled his aspirations and contributed to his community.

Now, he enjoys a fulfilling career in the homestay industry-a feat he accomplished by building rapport with goal-oriented people and taking advantage of opportunities. He outlined sound business principles that drove him to establish a profitable enterprise with no upfront capital. Using these same principles, any of our students can emulate Bruce and flourish in their career.

As detailed in the table below, Bruce exemplifies the ten modules taught in our coursework. By following his example and adhering to the success principles outlined below, our team is convinced that diligent, purpose-driven students can thrive upon release.

Values: We must define success.We must define our measure of success and constantly strive towards it. This involves breaking the mold and challenging traditional pathways, just as Bruce began seeking ways to escape poverty. Looking for a better future, Bruce chose to get an education through the Navy.  
Goals: We must set clear goals that align with our definition of success.Our students must set clear goals and have a solid plan. vAs Bruce moved from a two-year to a four-year degree, he had a clear goal of building a successful life by acquiring assets.
Attitude: We must make a commitment with the right attitude.We must have positive attitude and a 100% commitment to achieving success. This commitment should span all aspects of your life, from personal to professional endeavors.  
Aspiration: We must see ourselves as being something more than the challenges we currently face.Our listeners should aspire to achieve more and continuously improve. Throughout his life, Bruce sought to climb higher and build better pathways, embodying this spirit of aspiration.
Action: We must take incremental action steps.Success often requires active pursuit. We should not wait for opportunities to come our way; instead, go out and create them ourselves. This is shown when Bruce actively finds opportunities and created plans as he initiated new business ventures.  
Accountability: We must hold ourselves accountable.We must hold ourselves accountable for our actions and commitments. Throughout his career, Bruce held himself accountable to himself, his partner, and those who believed in him.  
Awareness: We must stay aware of opportunities.Opportunities often present themselves to those who are prepared and alert, as Bruce was when he spotted the right opportunities in his real estate career.  
Authenticity: We must be authentic.We must be genuine and true to our core. This requires executing a plan consistently, as Bruce did throughout his journey.  
Achievement: We must celebrate small victories.Our students should celebrate every little achievement because they lead to bigger opportunities. Bruce’s celebration of small accomplishments eventually led him to significant wealth accumulation.
Appreciation: We must show appreciation for the blessings that come our way.We must express gratitude for the blessings that come your way. Bruce shared his inspiring story and volunteered his time to help others, displaying a sense of gratitude and willingness to give back.

To facilitate learning, this lesson plan includes supplementary documents with pertinent information. Each complements the material already outlines by providing additional resources, particularly for those interested in entrepreneurship:

  • The Homestay Journey: A Timeline
  • Appendix A: Related Reading
  • Appendix B: Supporting Organizations
  • Appendix C: Potential Careers

Across the United States, the issue of mass imprisonment wreaks havoc on individuals and their communities, intensifying cycles of generational poverty, repeat offenses, and family disruptions. At Prison Professors, our mission is to put an end to this damaging cycle.

Following Bruce’s example, we encourage our students to adopt a mindset focused on concrete goals, hone their abilities, and take advantage of the opportunities that await them.

Let’s learn from him together and work towards earning our freedom!

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. Following Bruce’s example, can you think of a simple product or service in your own environment that could potentially be profitable?
  2. How does Bruce’s message about taking advantage of second chances after experiencing failure resonate with you?
  3. How does Bruce demonstrate resilience, and how can you apply that lesson to overcome your challenges?
  4. Does this story inspire you to become an entrepreneur? Why or why not?
  5. How do you think Bruce’s critical thinking skills led him to identify market needs and opportunities for profit?
  6. When coordinating a project or team, like Bruce in his wealth management venture, what strategies might you use to ensure effective collaboration?
  7. What skills can you develop to identify business needs and opportunities, and how can developing this skill lead you to succeed?
  8. What are some ways that you could improve your resilience, financial acumen, and risk assessment skills, inspired by Bruce’s story?
  9. What does the diversification in Bruce’s business teach you about the importance of having multiple income sources and versatile skills?
  10. Considering Bruce’s commitment to community engagement, how could giving back to the community play a part in your personal success and fulfillment?

The Homestay Journey: A Timeline

To clarify the rapid growth of the homestay venture operated by Bruce and his wife, the timeline below illustrates and dates key events in their business journey.

Business Growth Timeline
2018 A cabin in the woods

Description automatically generated with low confidenceBruce and his wife purchase five cabins, marking their entry into the real estate industry. They meticulously calculate potential costs and risks to establish a solid business model, including provisions for emergencies and periods of low cabin occupancy.
2018-2023 (Ongoing) A person and person shaking hands in front of a house

Description automatically generatedBruce and his wife negotiate a five-year financing deal with the previous owner. They manage a monthly payment of around $3,000 and simultaneously strive to increase the cabins’ value while paying off the debt. They successfully double their revenue by the third year through active involvement, building relationships, and hands-on business development.
Around 2019 (Year 2) A picture containing outdoor, boat, sky, water

Description automatically generatedTaking advantage of the solid reputation earned through their cabin business, Bruce and his wife venture into a more profitable boat rental business. This new addition to their portfolio makes them more revenue in three months than a year’s worth of cabin rentals.
2023 (Year 5) A hand holding a key with a house keychain

Description automatically generated with medium confidenceBruce and his wife approach full repayment of their initial debt. The cabins, now significantly more valuable than their original purchase price, contribute to the increased value of their LLC. Their boat rental business continues to thrive. A grocery store deli bait shop has been added to their diverse portfolio. They also give back to their community, partnering with a local food pantry.


  • Adage (noun): A proverb or short statement expressing a general truth.
  • Airbnb (noun): An online marketplace that connects people who want to rent out their homes with people who are looking for accommodations in that locale.
  • Attain (verb): To succeed in achieving something after trying for a long time.
  • Avail (verb): To use or take advantage of something.
  • Capital (noun, finance): Wealth in the form of money or other assets owned by a person or organization or available for a purpose such as starting a company or investing.
  • Cohesive (adjective): Working or fitting together well.
  • Community Engagement (noun): The process by which community benefit organizations and individuals build ongoing, permanent relationships for the purpose of applying a collective vision for the benefit of a community.
  • Complement (verb): Add to (something) in a way that enhances or improves it; make perfect.
  • Creative Financing (noun, real estate): A term used broadly to refer to financing techniques that involve non-traditional means of funding a real estate purchase.
  • Destitution (noun): Extreme poverty.
  • Dialogue (noun): Conversation between two or more people as a feature of a book, play, or movie.
  • Dictate (verb): To give orders or instructions.
  • Due Diligence (noun, real estate): An investigation or audit of a potential investment to confirm all material facts, such as reviewing all financial records.
  • Economic Mobility (noun): The ability of an individual, family or some other group to improve (or lower) their economic status.
  • Eligibility (noun): The state of having the right to do or obtain something through satisfaction of the appropriate conditions.
  • Endeavor (noun): An attempt to achieve a goal.
  • Equity (noun, finance): The value of an ownership interest in property, including shareholders’ equity, in a business.
  • Erudite (adjective): Having or showing great knowledge or learning.
  • Exemplar (noun): A person or thing serving as a typical example or excellent model.
  • Exemplify (verb): To be a typical example of.
  • Expansive (adjective): Covering a wide area in terms of space or scope; extensive or broad.
  • Feat (noun): An achievement that requires great courage, skill, or strength.
  • Financial Literacy (noun): The understanding of various financial areas including topics related to managing personal finance, money and investing.
  • Flipping (verb, real estate): The practice of buying property and reselling it quickly, usually after making improvements to increase its value.
  • Game-changer (noun): A newly introduced element or factor that changes an existing situation or activity in a significant way.
  • GI Bill (noun): A law that provides educational assistance to service members, veterans, and their dependents.
  • Hone (verb): To refine or perfect something over a period of time.
  • Homestay Industry (noun): A type of tourism and/or study abroad program that allows the visitor to rent a room from a local family to better learn the local lifestyle.
  • Infer (verb): To deduce or conclude information from evidence and reasoning rather than from explicit statements.
  • Inventory (noun): A complete list of items such as property, goods in stock, or the contents of a building.
  • Kindle (verb): To arouse or inspire (an emotion or feeling).
  • Knack (noun): An acquired or natural skill at performing a task.
  • Lucrative (adjective): Producing a great deal of profit.
  • Misguided (adjective): Having or showing faulty judgment or reasoning.
  • Mundane (adjective): Lacking interest or excitement; dull.
  • Passerby (noun): A person who happens to be going past something, especially on foot.
  • Pertinent (adjective): Relevant or applicable to a particular matter.
  • Potent (adjective): Having great power, influence, or effect; strong and effective.
  • Proficiency (noun): A high degree of competence or skill; expertise.
  • Refurbish (verb): To renovate or redecorate, especially a building or room.
  • Safety Net (noun): A safeguard against possible hardship or adversity.
  • Scarcity (noun): The state of being scarce or in short supply; shortage.
  • Sibling (noun): Each of two or more children or offspring having one or both parents in common; a brother or sister.
  • Succumb (verb): To fail to resist pressure, temptation, or some other negative force.
  • Thorough (adjective): Complete with regard to every detail; not superficial or partial.
  • Venture (noun, business): A new business enterprise that’s typically risky but has the potential for significant profit. It often refers to a joint project in which different parties or companies participate.
  • Vocation (noun): A strong feeling of suitability for a particular career or occupation.

Appendix A: Related Reading

Based on Bruce’s professional journey in the homestay industry, real estate, and sales, we have curated a list of books for any of our students interested in these fields. The authors of these books bring a wealth of experience and unique perspectives from their respective fields, offering practical insights, proven strategies, and inspiring stories to equip you for your entrepreneurial journey.

Homestay Industry Books
“The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions… and Created Plenty of Controversy” by Leigh Gallagher. The author, an assistant managing editor at Fortune, provides a comprehensive inside look at how Airbnb became one of the world’s most innovative companies. This book delves into the unique business model of Airbnb and presents a fascinating exploration of its challenges and triumphs.   “The Home Stay Guide: Practical Advice for Airbnb and Homestay Hosts” by Gabriela Domicelj and Derek Young The authors, experienced global nomads and successful Airbnb hosts, share their experiences and insights in this practical guide for anyone interested in the homestay industry. This book gives invaluable advice on setting up and managing a homestay business.   “Every Airbnb Host’s Tax Guide” by Stephen Fishman. A comprehensive guide by attorney Stephen Fishman on how to handle local and federal taxes as an Airbnb or other short-term rental host. A must-read for anyone getting into the homestay business to avoid legal pitfalls and optimize their tax situation. “Optimize YOUR Airbnb: The Definitive Guide to Ranking #1 in Airbnb Search” by Daniel Vroman Rusteen A former Airbnb employee, Rusteen gives a comprehensive guide on how to stand out from the crowd and get your homestay business to the top of Airbnb’s search results.
Real Estate Investment Books
“The Book on Rental Property Investing: How to Create Wealth and Passive Income Through Smart Buy & Hold Real Estate Investing” by Brandon Turner. As an active real estate investor with nearly a decade of experience, Turner shares his knowledge in this comprehensive guide to building wealth through rental properties. It covers everything from finding and screening tenants to managing properties and dealing with unexpected issues. “The Millionaire Real Estate Investor” by Gary Keller, Dave Jenks, and Jay Papasan. This book by Keller, co-founder of Keller Williams Realty International, and his team is a thorough manual to investing in real estate. It provides strategies, models, and case studies from successful investors. “Rich Dad Poor Dad” by Robert Kiyosaki. In his best-selling book, Kiyosaki shares the story of his two dads: his real father, who was poor, and the father of his friend, who was rich. He contrasts their views on money and investing, emphasizing the importance of financial education. This book provides a good foundational understanding of investment and wealth-building principles. “Real Estate Investing For Dummies” by Eric Tyson and Robert S. Griswold. A practical, step-by-step guide to real estate investing, perfect for beginners. Tyson, a personal finance expert, and Griswold, a real estate professional, cover a wide range of topics from property valuation to financing options.
Sales Industry Books
“The Little Red Book of Selling: 12.5 Principles of Sales Greatness” by Jeffrey Gitomer. The author, a renowned sales consultant and trainer, distills his decades of sales experience into this concise, easy-to-read guide. It provides practical advice on all aspects of sales, from prospecting to closing deals.   “Influence: The Psychology of Persuasion” by Robert Cialdini. The author, a prominent psychologist and marketing expert, delves into the science behind persuasion in this landmark book. It’s not strictly a sales book, but its insights on how to persuade others to agree with you are invaluable for anyone in sales.   “The Little Red Book of Selling: 12.5 Principles of Sales Greatness” by Jeffrey Gitomer. The autor, a renowned sales consultant and trainer, distills his decades of sales experience into this concise, easy-to-read guide. It provides practical advice on all aspects of sales, from prospecting to closing deals.   “Influence: The Psychology of Persuasion” by Robert Cialdini. The author, a prominent psychologist and marketing expert, delves into the science behind persuasion in this landmark book. It’s not strictly a sales book, but its insights on how to persuade others to agree with you are invaluable for anyone in sales.

Appendix B: Supporting Organizations

This appendix provides a comprehensive list of organizations and programs aimed at supporting justice-impacted individuals in their pursuit of various industries. These resources offer a range of services, including entrepreneurship training, employment readiness, vocational training, job coaching, mentorship programs, and housing assistance. Whether students are interested in the homestay industry, real estate, sales careers, or any other field, these organizations can provide valuable guidance and support on their journey towards success.

The Last Mile: This organization works with justice-impacted individuals, teaching them various skills, including entrepreneurship. While they’re mostly known for their coding program, the skills learned are applicable to any industry, including the homestay and real estate industry. (   Prison Entrepreneurship Program (PEP): This organization aims to connect justice-impacted individuals with business executives, entrepreneurs, and politicians. Their program covers entrepreneurship, employment readiness, and re-entry, which could be helpful for those interested in any industry.(   Center for Employment Opportunities (CEO): CEO provides immediate, effective, and comprehensive employment services to individuals with recent criminal convictions. Their program includes job coaching, vocational training, and job placement, which could be beneficial for those interested in the homestay industry, real estate, and sales. (   National HIRE Network: Established by the Legal Action Center, the National Helping Individuals with criminal records Re-enter through Employment (HIRE) Network is both a national clearinghouse for information and an advocate for policy change. They might provide guidance and resources for justice-impacted individuals aiming to start in any business or industry. (
Homestay Industry
Help For Felons: This organization provides resources and support for individuals with criminal records, including assistance with finding housing opportunities such as homestays. (   The Second Chance Project: They focus on providing opportunities for justice-involved individuals, including training and mentorship programs for those interested in the hospitality industry, which includes homestays. (   The Last Mile: This organization offers technology training and entrepreneurship programs for incarcerated individuals, which can be beneficial for those looking to start a homestay business. (
Real Estate
The Fortune Society: They offer a variety of services for individuals with justice involvement, including housing assistance and vocational training. They may be able to provide guidance on getting involved in the real estate industry. (   The Prison Entrepreneurship Program: While primarily focused on entrepreneurship, they also offer resources and guidance on various career paths, including real estate. (   The Real Estate Apprentice Foundation: This organization provides training and mentorship programs specifically for justice-impacted individuals interested in pursuing a career in real estate. (  
Sales Careers
The Center for Employment Opportunities (CEO): They specialize in providing employment services for individuals with criminal records and offer job readiness training, including sales skills development. (   The Safer Foundation: They offer a range of support services for justice-involved individuals, including job training and placement assistance, which can be valuable for those interested in sales. (   The Second Chance Employment and Entrepreneurship Expo: This annual event brings together employers, mentors, and resources specifically geared towards individuals with criminal records looking to enter the job market, including sales opportunities.

Appendix C: Potential Careers

Based on Bruce’s story, a wide range of potential job opportunities can be identified for justice-impacted individuals, showcasing their resilience, skills, and determination to succeed. This appendix highlights several viable career paths based on the experiences of individuals like Bruce, who transformed their lives and embarked on successful entrepreneurial journeys.

  • Real Estate Investment and Flipping: Bruce started his entrepreneurial journey in the real estate industry, specializing in buying and flipping properties. This type of venture requires knowledge of the real estate market, negotiation skills, and the ability to identify profitable investment opportunities.
  • Wealth Management Consultation: Bruce recognized a gap in wealth management for affluent clients and created a process to connect professionals and establish a more cohesive approach. Justice-impacted individuals with experience in finance or wealth management could offer consulting services to help clients effectively manage their wealth and coordinate with various professionals.
  • Financial Literacy Education: Bruce identified the need for financial literacy among small business owners and individuals with limited capital. Justice-impacted individuals with knowledge of finance and a passion for education could start a business focused on providing financial literacy workshops, seminars, and resources to help others learn how to grow their wealth.
  • Short-term Rentals/Hospitality Business: Bruce and his wife ventured into the short-term rental industry by repurposing cabins into Airbnb-style rentals. Justice-impacted individuals could explore opportunities in the hospitality sector by managing short-term rentals, such as vacation homes, cabins, or apartments. This type of job requires property management skills, marketing expertise, and a focus on customer service.
  • Boat Rentals and Camp Store Operation: Bruce and his wife expanded their business to include boat rentals and operating a camp store. Justice-impacted individuals with an interest in outdoor recreation and retail management could explore opportunities in these areas, providing services and products to tourists and local communities.
  • Nonprofit Work and Community Engagement: Bruce and his wife actively engage in nonprofit work and believe in community engagement as a vital part of running a successful business. Justice-impacted individuals can pursue job opportunities in the nonprofit sector, focusing on community outreach, advocacy, or program management to make a positive impact.

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