Preparing for Success: Matt 

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Title: Preparing for Success after Prison with Matt


  • Matt drove himself to become a star athlete and business champion through self-discipline, adaptability, and resilience. He teaches our students crucial lessons concerning the success principles that drove his achievements and shares key business insight in the realms of sales, real estate, and property management. We also learn the value of interpersonal skills, persuasive communication, and active listening from the interview.


  • Students should improve their understanding of the importance of perseverance, awareness of opportunities, and communication skills. Our listeners should also garner key business insights from Matt based on his career. Other crucial takeaways relate to personal branding and coping with rejection and setbacks.

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 interacts with people who have showcased remarkable grit and determination in their journeys, aiming to provide actionable insights for our students. Today, we spotlight Matt, who transitioned from passionately pursuing athletics to thriving in the bustling world of business, exemplifying both adaptability and foresight.

Exploring Matt’s narrative, we learn about his professional milestones and the key personality traits that drove his success, including unwavering discipline and a knack for building relationships with stakeholders. As he walks us through his career path, he offers valuable business insights and personal branding pointers. Using Matt as a case study, we can better navigate our paths, harnessing inspiration to shape brighter futures.


Born and raised in Madison, Wisconsin, Matt exhibited several hallmarks of success from a young age: competitiveness, tenacity, and self-assurance. An outdoorsy young man, he embarked on an array of athletic endeavors, such as soccer, baseball, football, skiing, and aquatic sports. Yet, among these, hockey stood out. The pace, energy, and competitive nature of the game deeply resonated with him.

In a bold move during his senior year of high school, Matt relocated to live with a surrogate family in Iowa to play in a more demanding hockey league, aiming to sharpen his skills for collegiate-level play. He prioritized earning good grades, understanding that pursuing his passion would require exceptional grades for admission into a top university. Matt’s dedication bore fruit. He secured a spot at the University of Wisconsin, a prestigious Division One school, reflecting the university’s top-tier athletic program and scholarship offerings.

Matt longed for an athletic career yet continued to make pragmatic decisions for his future. While his dreams of professional hockey danced in his mind, he was grounded enough to prioritize his education, realizing that he would have to develop skills outside the ice rink to ensure his long-term success.

Image 1: As a hockey star, Matt learned lessons in teamwork and communication, driving his later business success.

Midway through college, Matt developed an interest in business. Joining the business school at the University of Wisconsin, he discovered an affinity and knack for sales. Introduced to the corporate world through his father-in-law and other networks, Matt saw sales as a pivotal starting point for anyone aspiring to delve deeper into the corporate sphere. Sales went beyond transactions; it was about understanding a company’s core by directly connecting with its clientele. Fueled by his passion, Matt graduated with a degree in agricultural business management.

Yet, transitioning from the hockey rink to boardroom meetings came with significant challenges. Matt had to navigate a change in identity, from being an athlete to a salesperson. As he delved into the world of sales, he realized that many of the transferable skills he honed on the ice—determination, discipline, and the ability to foster relationships—were crucial in his new role. Matt’s journey shows us that with determination and adaptability, skills from one domain can transition and find relevance in another. Based on his experience, ask yourself: What skills do I have and how can I repurpose them as I pursue a new career or advance my education?

Matt’s early life is a testament to the power of resilience, adaptability, and a vision for the future. No matter where we come from or the challenges we’ve faced, the ability to translate skills, remain open to growth, and be anchored by clear goals can guide us toward unforeseen opportunities. Our backgrounds, experiences, and passions shape us, but don’t define our limits.


Having left prison over a decade ago, I seek role models who exemplify success principles that can lead anyone to thrive in society. I routinely adhere to the guidance from leaders like Matt, who offer invaluable advice on how people can overcome seemingly insurmountable challenges through a goal-oriented attitude, relentless work ethic, and investment in their skills.

Matt’s journey offers fundamental lessons in active listening and interpersonal skill development. Recalling the adage that “people buy from people,” Matt honed robust talents in communication and teambuilding as an athlete, abilities that later drove his success as a salesperson. As a company representative, he could sell products if he first sold himself. To gain the trust of teammates and customers, Matt developed a professional and friendly demeanor as a form of personal branding. Following his example, we must become effective communicators by refining our listening skills, understanding the needs and desires of others, and presenting ourselves with authenticity and integrity.

A crucial step toward engaging well with other people involves asking open-ended questions. Rather than dominate conversations, we should remain inquisitive when speaking with others to show a genuine interest in the other person. Socratic questioning, the art of asking thought-provoking questions to share ideas, can serve as a valuable method to build relationships with others. By using Socratic questioning, we encourage deeper thinking and reflection, as well as allow others to express their thoughts and beliefs fully.

Another vital communication technique we can adopt is the Purpose, Process, Payoff method (also known as the 3Ps), a staple in cold calling. As stated by Matt, salespeople use this technique to initiate discussions with a clear intent, ensure a structured approach, and emphasize shared advantages to ensure transparency and a purposeful direction. As detailed in the infographic below, our listeners can apply each step to help rebuild their lives as they seek new employment opportunities.

For someone looking for employment, the 3Ps principle could apply in an interview as outlined in the table below.

Purpose:  What: “I’m here to apply for the position of sales representative.” Why: Clearly state the intention right from the beginning, eliminating ambiguity. Example: “I want to meet with you today is to discuss the sales representative position and demonstrate how my unique experiences can bring value to your team.”
Process:  What: Lay out qualifications, experience, skills, and address any potential gaps in the employment history. Why: Provide a structured explanation of one’s professional journey. Example: “After completing my degree in marketing, I took some time to reflect and grow personally. During this period, I volunteered at a non-profit, honing my sales skills. I’ve also attended workshops to stay updated with the latest sales techniques.”
Payoff:  What: Emphasize the unique perspective and resilience they bring. Why: Differentiate oneself from other candidates by highlighting personal growth and the lessons learned from past experiences. Example: “Given my journey, I’ve developed a resilience and perspective that allows me to connect with a diverse range of customers, and I believe this makes me a valuable asset for your team

Just as Matt reinvented himself—transitioning from a dedicated athlete to a successful businessperson—we are also capable of transformation. Everyone has a unique set of skills, experiences, and insights, and even those stemming from adversities can be turned into strengths. Let’s follow his example and harness our past—with all its lessons and experiences—and let it guide us into a brighter and more promising future.

  • How do you believe Matt’s athletic career helped him cultivate skills in communication and teambuilding?
  • What tough choices have you made for a better future, like Matt’s move to Iowa?
  • Based on Matt’s example, how can effective communication aid in rebuilding relationships and trust?
  • What are examples of questions you can ask in a job interview using the Socratic method?
  • How do you believe the Purpose, Process, Payoff model can help you as you seek a new career?


Matt’s first professional position was with Ricoh Business Solutions, a renowned global document solutions firm. Assigned a specific territory in Madison, his daily routine revolved around cold calling to sell and build relationships with potential clients. While he regularly faced rejection as a salesperson, Matt developed strategies to boost his success. He developed a keen sense of persistence and focused on identifying key decision-makers, with success often coming after repeated follow-ups.

An integral part of Matt’s development at Ricoh was the support he received from his sales managers. Beyond serving as his supervisors, these managers were mentors who played an instrumental role in charting his career trajectory. Matt acclaims these managers for their proactive approach, setting clear objectives, and assisting in designing a pathway to achieve these goals.

However, while the experiences at Ricoh were invaluable, Matt soon transitioned to the agricultural sector, a decision influenced by both his degree in agricultural business management and the burgeoning opportunities in this sector around 2008. He soon found himself associated with Bayer. While the conglomerate is most famous for its role in pharmaceuticals, it is also the world’s largest agricultural company.

Image 2: Matt developed solid communication and people skills to succeed as a salesperson.

At Bayer, Matt’s responsibilities involved selling seeds and crop protection chemicals to help farmers produce quality crops. Despite being a manufacturer and research and development hub, Bayer’s distribution network was intricate. The company sold primarily to large distributors, who liaised with local farmers or smaller retailers. As for Matt, his role at Bayer had him interacting across this spectrum, although he dedicated a significant allotment of his time with major distributors. Matt defined his success as meeting and consistently exceeding sales targets, backed by a solid business plan.

Eager to seek new opportunities, Matt eventually ventured into another industry: real estate. He became acquainted with the real estate market due to his numerous relocations in his sales roles, sparking an interest that he turned into a novel career experience. He started selling homes, gradually building up a portfolio of rental properties.

The competition in the real estate market was fierce, with several agents vying for the attention of potential clients. Establishing personal connections and positioning oneself as the preferred agent became crucial. Likewise, many of our students may face intense competition on the job market. Yet following Matt’s example, our listeners can distinguish themselves by starting as early as possible to build professional networks and honing their interpersonal and communication skills.

Let’s consider Matt’s strategy to find new clients. His success depended on personal networking and using social media sites to connect with other agents and promote his listings. His persuasive communication skills were also paramount to his journey, as he built rapport with clients through genuine engagements, open-ended questions, and active listening skills. As yourself: What personal networks can I build to ease my transition into a career? What skills can I start developing and strengthening to streamline my reintegration?

Image3: Like his sales roles, communication was paramount to Matt’s success in real estate.

Still keen to explore new ventures, Matt later began working in property management, which he described as handling all facets of a property without owning it. This role included maintenance, tenant management, and handling contracts. When compared to his previous real estate role, property management offered Matt a more stable and predictable environment, less susceptible to volatile market conditions.

He also saw potential in flipping homes— purchasing such properties at a lower price due to their outdated nature and then investing in updates and renovations for a higher resale price. This practice appealed to Matt as a way to help people find updated and comfortable homes while also securing a profit for his efforts.

Throughout his career, whether selling office products, agricultural solutions, homes, or managing properties, Matt’s story is a testament to adaptability, continuous learning, and the power of building genuine relationships. We must follow his example of remaining aware of opportunities and seeking rapport with others to ensure success in our journey.

Business Insights

As Matt discussed his career path, we gleaned critical insight into business concepts in sales, real estate, and property management.


  • Definition: Prospecting refers to an organized approach of identifying potential customers or clients for a product or service.
  • Example: Consider Matt’s strategy within his sales and marketing context. In real estate, prospecting involves identifying potential homeowners considering the sale or rental of their properties. Similarly, Matt used specific methods to identify potential customers in agriculture. For our students, the application of prospecting techniques might involve analyzing neighborhoods, studying online property forums, or surveying local community interest in real estate trends.

Marketing vs. Sales:

  • Definition: Marketing encompasses a broad set of activities focused on understanding consumer needs, developing strategies, and creating brand awareness. Sales, conversely, centers on the direct transaction and interaction with the end consumer to sell the product or service.
  • Example: For a real estate professional like Matt, marketing entails listing properties on various platforms, hosting open-house events, and creating promotional materials. Sales, in contrast, come into play when persuading a potential buyer to finalize a purchase.

Lead Generation:

Definition: Lead generation fosters consumer interest in services or products.

Example: To provide a real estate context, consider a scenario where agents attend local community events, such as home expos or neighborhood gatherings. Engaging with attendees and collecting contact information creates a pool of leads that can later be nurtured into prospective clients.

Recurring vs. One-Time Sales:

  • Definition: Recurring sales refer to predictable and regular purchases of a product or service, while one-time sales denote infrequent, typically more substantial, transactions.
  • Example: Reflect on Matt’s explanation of the agricultural sales model, where farmers buy seeds with predictable frequency—these represent recurring sales. Applying this to a real estate scenario, selling a residential property represents a one-time sale, while property management services, involving periodic fees, exemplify recurring sales.

Personal Branding

  • Definition: Personal branding is the strategic positioning and marketing of oneself, converging unique skills, experiences, and individual characteristics.
  • Example: Delve into Matt’s professional trajectory. His knack for strategic sales aspects and his commitment to enhancing customer success together shape his personal brand. Students seeking a career in real estate might cultivate their personal brand by emphasizing attributes like reliability, knowledge of local property analytics, or a specialized approach to assisting particular segments, such as first-time homebuyers.

Matt’s journey illuminates a path of empowerment and a means to rebuild our lives. By attaining proficiency in the business concepts discussed, we can potentially open doors to new careers and attain a meaningful and lucrative livelihood. Let’s follow Matt’s example to forge a brighter, self-reliant future.


Our students should reflect on how Matt’s tenacity forged his pathway to success. A crucial takeaway from Matt’s journey from sales to real estate is the power of self-discipline. His jobs required him to adapt to fluctuating schedules and frequently travel or work remotely. He persisted against challenges through a steadfast focus on his goals, constantly seeking growth even when facing daunting challenges.

As we concluded our conversation, he asserted that discipline was the “number one” factor in his success throughout his journey. Following his example, must anchor ourselves through self-discipline, ensuring stability in both calm and tumultuous times.

Matt’s story also illuminates the power of resilience. Confronted with rejection, he remained undeterred, finding purpose in every career role he undertook. It’s a lesson for our students: setbacks are steppingstones, and every challenge is a new learning curve on the path to personal and professional growth.

We also gleaned valuable insight on the importance of mentorship. Success seldom comes without guidance and support. Matt’s achievements show us the vital role of mentors and a strong support network. These figures, with their experience and insights, not only guided his career decisions but also enriched his personal and professional growth. For our students, mentors can act as guiding lights, illuminating potential pathways and providing direction on our chosen journeys.

Matt also teaches us the importance of embracing opportunities. His ability to identify, seize, and nurture unexpected opportunities molded his success in distinct businesses. Whether it was his transition from Ricoh to Bayer or his foray into real estate, he remained agile and open to possibilities. The lesson from his example is clear: life’s unplanned events, when approached with an open heart and mind, often become the most enriching experiences.

Lastly, Matt reminds us of the importance of being authentic. In every professional engagement, gaining the genuine trust of others is crucial for relationship building. In the world of real estate, Matt built authentic connections with clients and peers. His focus went beyond the simple transaction, as he sought to build lasting relationships. This level of authenticity, rooted in genuine intent and trust, goes beyond business—it creates a shared space of mutual respect and value.

  • Based on Matt’s example, what mechanisms can you develop to deal with rejections and setbacks as you seek to rebuild your life?
  • How do you believe mentorship shaped Matt’s career journey and how can seeking mentorship benefit you?
  • How did Matt distinguish himself from competitors, and what skills can you develop to do the same?
  • How can developing a strong personal brand help you stand out as you seek job and business opportunities?
  • How do you believe Matt used his math and critical thinking skills to succeed in his different career roles?


Matt’s odyssey—from the ice rinks of Madison to the complex corporate arenas—is an enlightening tale of tenacity, adaptability, and growth. His foundation in sports fostered essential life skills that empowered his later success in the business world. His inherent resilience and insatiable hunger for seizing opportunities should inspire all our students. By following his example, our students can begin rebuilding their lives and earning their freedom.

His professional experiences at Ricoh and Bayer, and later in real estate and property management, demonstrate the indispensability of mentorship, personal branding, and genuine relationship-building for career development. Based on his example, our students should immediately start expanding their professional networks and begin developing their communication and interpersonal skills to increase their odds of success.

Matt’s story serves as a vivid reminder that with the right attitude, skills, no matter where honed, can be repurposed to overcome challenges and reach the pinnacles of success.

Each chapter of Matt’s story is aligned with the ten modules of our coursework:

Values: We must define success.Matt exhibited a clear definition of success early on, demonstrated by his determination to play hockey. He understood the sacrifices and the effort required, like leaving home during high school and maintaining good grades to join a Division One university.
Goals: We must set clear goals that align with our definition of success.In his sales career, Matt showed a strong commitment. He knew that success wouldn’t come immediately and that he might need multiple interactions to establish a productive relationship.
Attitude: We must make a commitment with the right attitude.Regardless of the domain—be it hockey or sales—Matt consistently maintained the right attitude by remaining committed to his goals and aspirations.
Aspiration: We must see ourselves as being something more than the challenges we currently face.Throughout his journey, Matt had clear aspirations. He always envisioned his next step, be it transitioning from being a hockey player to becoming a sales professional and later, a sales manager.
Action: We must take incremental action steps.He always believed in taking concrete actions. He actively sought ways to improve his skills, such as learning the art of asking open-ended questions.
Accountability: We must hold ourselves accountable.Matt emphasized the importance of self-motivation and being accountable, especially when faced with distractions like working from home. He believed in setting a direction and sticking to it.
Awareness: We must stay aware of opportunities.Matt was adept at scanning his environment for opportunities. He consistently looked for potential clients, used platforms like social media to boost his visibility, and ensured he stayed connected with relevant stakeholders.
Authenticity: We must be authentic.Everything Matt spoke about resonated with sincerity and authenticity. He believed in having a roadmap, setting clear priorities, and effectively using tools and tactics to achieve his goals.
Achievement: We must celebrate small victories.Matt valued every achievement, irrespective of its scale. He fondly recollected skills and milestones from his past roles, underscoring the importance of acknowledging and celebrating every success.      
Appreciation: We must show appreciation for the blessings that come our way.Matt’s contributions, especially his volunteering efforts for our course and his outreach to incarcerated individuals, spoke volumes about his sense of gratitude and appreciation for the opportunities he had and the knowledge he acquired.

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

  • Student Skill-building Exercise: Personal Branding
  • Student Skill-building Exercise: Math, Critical Thinking, and Communication Skills
  • Glossary
  • Appendix A: Related Reading and Resources
  • Appendix B: Supporting Organizations
  • Appendix C: Potential Careers

Our team at Prison Professors seeks to motivate students to earn their freedom and avoid the pitfalls of recidivism. Our goal is to fight against mass incarceration, one of the biggest social injustices in the country. Through learning from leaders like Matt and adhering to our success principles, all our students can transform their lives and remain on the pathway to success.

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. Have you ever transferred skills from one part of your life to another, as Matt did from sports to sales?
  2. Have you had a mentor or guiding figure like Matt had at Ricoh? How did they influence you?
  3. In what areas of your life has perseverance made a difference?
  4. Using Matt’s example, how do you distinguish yourself when you’re up against competition?
  5. How can becoming proficient at the Purpose, Process, Payoff method help you sharpen your critical thinking and communication skills?
  6. In what areas of your life has perseverance made a difference?
  7. Does Matt’s story inspire you to explore sales, real estate, or property management? If so, why?
  8. How do you believe honing your math, critical thinking, and communication skills could help you succeed in a field like sales or real estate?
  9. Why is building genuine relationships valuable in both personal and professional arenas?
  10. Other than those listed, in what ways does Matt’s life story reflect our ten coursework modules?

Student Skill-building Exercise: Personal Branding

Personal branding is the compass that directs our professional journey, spotlighting our strengths, experiences, and unique values. It’s about self-awareness and presenting oneself authentically to the world. For many, it’s a tool to reshape narratives and carve out a distinct space in diverse arenas. Dive into these five pivotal steps to mold your personal brand and ensure your story shines brightly.

Student Skill-building Exercise: Math, Critical Thinking, and Communication Skills

Venturing into sales, real estate, and property management requires more than just foundational knowledge; it demands hands-on practice and application. The following exercises are designed to bolster your math, critical thinking, and communication skills — three pivotal components of these industries. These scenarios mirror real-world situations you might encounter, allowing you to hone your capabilities and prepare for actual challenges in your chosen career. Dive in, and remember: practice makes perfect!

Math Skills:

Property Profit Calculation:

Scenario: You’ve sold a property for $350,000. You initially bought it for $250,000 and spent $40,000 on renovations. Calculate your total profit.

Solution: Profit = Sale Price – (Purchase Price + Renovation Costs).

Mortgage Interest Calculation:

Scenario: If you take out a mortgage of $200,000 at an annual interest rate of 5% to be repaid over 15 years, calculate the simple interest for the first year.

Solution: Interest = Principal x Rate.

Commission Calculation:

Scenario: If you sell a house for $500,000 and your commission rate is 3%, how much will you earn from the sale?

Solution: Commission = Sale Price x Commission Rate.

Critical Thinking Skills:

Property Value Assessment:

Scenario: Two properties are in the same area. Property A is 2,500 sq.ft. with 3 bedrooms and is priced at $450,000. Property B is 3,000 sq.ft. with 4 bedrooms and costs the same but is next to a noisy highway. Which is a better buy and why?

Investment Decision:

Scenario: You have $100,000 to invest. Option A is to renovate a property, increasing its value by 20%. Option B is to buy a new property that you predict will increase in value by 10% over the next year. Which option do you choose and why?

Tenant Dilemma:

Scenario: A potential tenant has a high-paying job but a poor credit history. Do you rent out your property to them? List the pros and cons and make a decision.

Communication Skills:

Objection Handling Role-play:

Scenario: A customer is hesitant to buy a property because they think it’s too old. Role-play a conversation where you address their concerns and try to persuade them.

Feedback Response:

Scenario: A client writes an email expressing dissatisfaction with a late property viewing appointment. Draft a suitable email response addressing their concerns while maintaining a professional tone.

Elevator Pitch Creation:

Scenario: You have a unique property that has a built-in office space, ideal for remote workers. Craft a 1-minute pitch to sell this property to potential buyers.


  • Acclaim (noun/verb) – public praise/approve
  • Acquaint (verb): To make someone aware of or familiar with
  • Actionable (adj.) – giving grounds for legal action; also, able to be acted upon
  • Adaptability (noun) – ability to adjust to new conditions
  • Affinity (noun) – a spontaneous liking or sympathy for someone or something
  • Agile (adj.) – able to move quickly and easily; flexible in thought & action
  • Aquatic (adj.) – relating to water
  • Burgeoning (adj.) – growing or increasing rapidly
  • Clientele (noun) – the clients of a professional person or shop, collectively
  • Cold calling (noun) – unsolicited calls made by salespeople
  • Collegiate (adj.) – relating to a college or its students
  • Conglomerate (noun) – a number of different things or parts that are put or grouped together to form a whole but remain distinct entities
  • Demeanor (noun) – outward behavior
  • Delve (verb) – to investigate or research deeply
  • Endeavor (noun/verb) – an attempt to achieve something/to try hard
  • Encompass (verb) – to surround, to include within a range
  • Exemplify (verb) – to be a typical example of
  • Exceptional (adj.) – unusual, not typical
  • Expo (noun) – exposition, large exhibition
  • Facet (noun) – one side of something many-sided
  • Flipping (real estate) (noun/verb) – buying property and quickly reselling it for profit
  • Fluctuating (adj.) – rising and falling irregularly
  • Foray (noun) – a sudden attack or incursion; an attempt at something new
  • Genuine (adj.) – truly what something is said to be
  • Glean (verb) – to gather bit by bit
  • Grounded (adj.) – well balanced and sensible; connected to reality
  • Hallmark (noun) – a mark indicating quality or excellence
  • Harness (verb) – put into use, utilize
  • Illuminate (verb) – to light up; to clarify or explain
  • Inaugurate (verb) – to make a formal beginning
  • Includable (adj.) – able to be included
  • Indispensability (noun) – the state of being essential or absolutely necessary
  • Insatiable (adj.) – impossible to satisfy
  • Insurmountable (adj.) – too great to overcome
  • Invaluable (adjective): Extremely useful or indispensable; beyond calculable or appraisable value
  • Initiate (verb) – to begin or introduce
  • Knack (noun) – a skill or an ability to do something easily and well
  • Liaised (verb) – to establish a working relationship
  • Milestone (noun) – an important stage or event
  • Novel (adjective): New or different from what is known or familiar
  • Nurture (verb) – to care for and protect
  • Odyssey (noun) – a long journey full of adventures
  • Paramount (adj.) – more important than anything else
  • Persistence (noun) – the quality of continuing steadily despite problems
  • Personal branding (noun) – the practice of people marketing themselves and their careers as brands
  • Pinnacle (noun) – the most successful point
  • Portfolio (real estate) (noun) – a range of investments or properties
  • Pragmatic (adj.) – dealing with things in a practical way
  • Proficiency (noun) – a high degree of skill
  • Rapport (noun) – a close and harmonious relationship
  • Real estate (noun) – property in the form of land and buildings
  • Recidivism (noun) – the tendency to relapse into a previous condition or mode of behavior
  • Reinvent (verb) – to change something so much it appears entirely new
  • Renowned (adj.) – famous, well-known
  • Resonate (verb) – produce or be filled with a deep sound; evoke or suggest emotions
  • Susceptible (adj.) – likely or liable to be influenced or harmed by something
  • Spectrum (noun) – a range of different positions, opinions, etc.
  • Surrogate (noun) – a substitute, especially a person deputizing for another
  • Transparency (noun) – the quality of being easy to see through or understand
  • Undeterred (adj.) – not discouraged or prevented from acting
  • Vie (verb) – to compete eagerly with someone in order to achieve something
  • Vivid (adj.) – producing powerful feelings or strong, clear images in the mind

Appendix A: Related Reading and Resources

Navigating the intricacies of careers in sales, real estate, and property management requires determination and a foundational understanding of the industry’s nuances. The following list of books has been curated to provide our students with a comprehensive overview and practical strategies in these fields.

Sales Careers
“SPIN Selling” by Neil Rackham Synopsis: An exploration of the SPIN (Situation, Problem, Implication, Need-payoff) technique, which has become a cornerstone in the world of sales strategy. “The Little Red Book of Selling: 12.5 Principles of Sales Greatness” by Jeffrey Gitomer Synopsis: Gitomer breaks down the essentials of selling with humor and zest, making the principles easy to remember and apply. “To Sell Is Human: The Surprising Truth About Moving Others” by Daniel H. Pink Synopsis: Pink discusses the art and science of selling in a modern context, shedding light on how everyone is in sales in some form or another. “Invisible Selling Machine” by Ryan Deiss Synopsis: Deiss discusses how to automate your marketing to “attract, nurture, and convert” customers without having to work 24/7. “Sell or Be Sold: How to Get Your Way in Business and in Life” by Grant Cardone Synopsis: Cardone emphasizes the role of selling in all areas of life and business, and how mastering the art of selling can enhance overall success.
Real Estate Careers
“The Millionaire Real Estate Agent” by Gary Keller Synopsis: A deep dive into the strategies used by successful real estate agents, detailing how to build and sustain a prosperous career in the industry. “Your First Year in Real Estate: Making the Transition from Total Novice to Successful Professional” by Dirk Zeller Synopsis: Ideal for beginners, this book provides valuable insights into navigating the challenges faced during the initial stages of a real estate career. “The Book of YES: The Ultimate Real Estate Agent Conversation Guide” by Kevin Ward Synopsis: A practical guide that provides the best scripts for real estate sales, emphasizing the importance of positive and persuasive conversations.
Property Management Careers
“The Property Management Tool Kit” by Mike Beirne Synopsis: An excellent resource for those interested in property management, offering actionable tips on effectively managing rental properties. “Every Landlord’s Guide to Managing Property: Best Practices, From Move-In to Move-Out” by Michael Boyer Synopsis: This guide covers the landlord’s essential tasks, focusing on time-saving and effective property management techniques. “Property Management Kit For Dummies” by Robert S. Griswold Synopsis: Part of the popular “For Dummies” series, this book breaks down the complexities of property management into digestible and comprehensible segments.

Appendix B: Supporting Organizations

Exploring the professional landscape can present unique challenges, but the right support can make all the difference. This appendix highlights organizations dedicated to assisting individuals looking for general career advice or who are interested in fields like sales, real estate, and property management. Whether you’re looking to develop skills, network, or find a starting point in a new career, these organizations provide valuable resources and guidance. Explore and connect with them to unlock new avenues for growth and success.

General Support
The Fortune Society Description: Offers a range of services to support successful reentry from incarceration and promote alternatives to incarceration. Website: Center for Employment Opportunities (CEO) Description: Provides immediate, effective, and comprehensive employment services to individuals with criminal convictions. Website: Defy Ventures Description: An entrepreneurship, employment, and character training program for currently and formerly incarcerated men, women, and youth. Website: The Last Mile Description: Provides training to help justice-impacted individuals develop professional and vocational skills, including business and entrepreneurship. Website:
Specialized Career Support
National Association of Sales Professionals (NASP) Description: A community of sales and influence professionals that offers training, certifications, and a platform to connect with peers. Website: Sales Enablement Society Description: Dedicated to promoting and elevating sales enablement as a profession. Offers events, resources, and networking opportunities. Website: National Association of Realtors (NAR) Description: The largest trade association in the U.S., NAR offers education, advocacy, and networking opportunities for real estate professionals. Website: National Association of Residential Property Managers (NARPM) Description: Dedicated to supporting residential property management professionals, NARPM provides educational and networking opportunities. Website:

Appendix C: Potential Careers

The fields of sales, real estate, and property management offer a diverse range of roles suitable for various skills and interests. Whether you’re passionate about building relationships, analyzing market trends, or managing property assets, there’s likely a role that aligns with your goals. This appendix provides an overview of potential career roles within these sectors, along with brief descriptions to help you identify the best fit for your aspirations.


  • Sales Representative: Tasked with selling products or services directly to consumers or businesses, they build relationships, understand client needs, and close deals.
  • Account Manager: A liaison between the company and its clients, they ensure customer satisfaction, handle queries, and manage client accounts to encourage repeat business.
  • Sales Development Representative (SDR): Focuses on generating leads, typically through cold calls or emails, and qualifying potential customers before passing them on to a sales team.

Real Estate:

  • Real Estate Agent: Assists individuals in buying, selling, or renting properties. They advise clients on market conditions, conduct walkthroughs, and negotiate contracts.
  • Property Appraiser: Determines the value of a property based on its condition, location, and market trends. This role is essential for setting sale prices or property taxes.
  • Real Estate Consultant: Offers specialized advice on real estate investment, market conditions, and property development. They help clients make informed decisions about real estate transactions.

Property Management:

  • Property Manager: Oversees the day-to-day operations of a property, ensuring maintenance, managing tenants, and handling rent collections.
  • Facilities Manager: Focuses on the maintenance, functionality, and safety of a building or complex, ensuring it meets the needs of its occupants.
  • Leasing Consultant: Works with potential tenants to find suitable rental properties, highlighting property features, and managing lease signings and renewals.

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