Blog Article 

 Homeless to Inspiring CEO 

Picture of Michael Santos

Michael Santos

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At an early age, Eric found himself homeless and unemployed. As the product of a broken marriage and the challenges that it creates, Eric turned his hardships into passions. Eric did not receive any formal college education and knew he wanted to get off the streets. He realized excellent communication, vocabulary, and critical thinking skills would help him achieve his goals. Eric eventually created multiple successful businesses, resulting in eight-figure revenues.

Objective of Learning Lesson:

  • In following Eric’s journey from homelessness to a millionaire, participants should learn the importance of developing excellent communication and critical thinking skills. Participants should also learn how to set daily goals for themselves to create the best outcome possible from their situation.

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 develop 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.

The team at Prison Professors expresses gratitude to Eric for sharing his experiences with us. Eric has demonstrated his fortitude in conquering tremendous obstacles and serving as a role model for facing up to the life and career challenges most people face upon leaving prison. 

Eric’s Back Story:

Eric lived the early part of his life in a challenging environment. His parents separated at an early age, and he often moved between living with them. Complications at home meant that Eric occasionally found himself without a place to live.

Eventually, Eric found himself living on the streets in Utah with zero financial resources. Eric experienced unsafe living conditions that he initially failed to comprehend. In-between homes and homelessness, Eric asked himself, “how am I in this situation”?  He realized he needed to change his mindset to get out of this situation.

Eric never gave in to life’s pressures. He eliminated the “why me” attitude, knowing that he could transform his life with perseverance, dedication, passion, and hard work. In time, such a mindset would lead to financial success—though it prosperity did come overnight. Eric’s willingness to work on any job, no matter how menial served as his key to getting off the streets.

Eric’s journey from homelessness to financial success does not translate easily to people that live in struggle. Homelessness, like incarceration, comes with personal and professional stigmas. Eric believed his own personal ‘failure’ story was just in his head. Every day he had to overcome his fear of failure, knowing that he could not make the same mistakes twice.

We can strengthen our confidence through personal training, taking steps every day to improve your situation. Choose one book to read, then another. You can learn new vocabulary words and how to use them correctly in a sentence. Eric’s financial successes are due to his ability to communicate appropriately and use his critical thinking skills to the best of his ability.

Even though Eric never attended college, a lack of a university degree did not stop him from learning. As we will discuss further below, Eric started each of his businesses with little to no knowledge of the industry. Eric knew each day was a new opportunity to think positively and to build confidence. The change in his life came slowly but through setting personally obtainable goals each day.

While homeless, Eric set a goal of obtaining any job he could find. Once Eric had one job, he learned everything about the job, the employer, and the industry. Then he set a goal to get a second job, also intending to learn about this business. Eventually, Eric set a goal of earning $100 per day. Sometimes Eric had to work three jobs to reach his goal.

At one point, Eric took on a third job at a local Denny’s restaurant. Eric took the graveyard shift, so he had a place to be in the middle of the night. The restaurant also provided him one hot meal. During the slow hours, Eric would sleep on the benches in the restaurant to prepare him for the next day. Eric worked on his communication skills in each conversation he had every day.

Eric believed he could bring value to others and he didn’t walk around with his baggage on his shoulders. He worked through his issues by being happy with his daily personal achievements and not sitting back and waiting for things to happen. Eric didn’t believe in ‘luck’ but believed in hard work to get him out of his situation. Eric’s confident determination to continue to work hard every day lead to his long-term financial success.


Eric’s motivational story should be an inspiration for anyone. Eric’s journey isn’t one of family money and an Ivy League education. Grit, determination, and getting back on his feet after failure are what led to Eric’s success. Setting small, personally achievable goals helped Eric succeed. Anyone in struggle can learn to succeed by following the principles that we can learn from Eric’s story.

When I listen to folks like Eric, I reflect on how I changed my mindset in prison. I knew I needed to change the way I spoke and acted. Stories like his helped me to appreciate that I had a great deal to learn. Specifically, I would need to work to develop an excellent vocabulary, better writing and oral communication skills, and exceptional critical thinking skills.

When the time came for me to leave prison, I didn’t want to be going into another prison wherever I lived because I didn’t know how to calibrate my life with the law-abiding society.  I choose to read books, to learn new words, to speak with as many positive people as I could find. Such decisions prepared me for success after 26 years in federal prison.

  • What thoughts and fears do you think Eric had while living on the streets?
  • How did Eric overcome his fears?
  • What thoughts and fears influence your life?
  • What can you do today to help you overcome those thoughts and fears?
  • How did the challenges Eric faced resemble the challenges that you now face?
  • In what ways would the strategies Eric used to overcome help you overcome challenges that you face?

Eric’s Early Decisions That Lead to Success:

As we heard from Eric’s story, he chose to make a change for himself. He did not want to live homeless anymore. Eric’s hard work at three low-paying jobs, including the graveyard shift at  Denny’s restaurant, eventually paid off.

Eric understood the value of having good communication and vocabulary skills. He learned while working in a butcher shop, in an ice cream parlor, delivering pizza, and working overnight as a waiter. Eric took every opportunity to have a conversation with someone to improve upon his communication skills. As Eric reached increasing levels of success, he also readjusted his goals. For instance, he increased his daily financial goal incrementally, from $100 to $300 per day.

By working hard at his three jobs and equally as hard on his communication skills, Eric demonstrated to others that he had value. When he showed his value to his employers, they awarded him more responsibilities with added pay. Eric learned to be happy with his daily achievements. Reaching your daily goals provides immediate feedback, impacting how you feel today and tomorrow.

Eventually, Eric’s hard work and determination paid off when restaurant customers approached Eric about a new business they started. These people saw Eric’s work ethic and excellent communication skills and offered him an equity partnership in a new restaurant they wanted to open in New York City. Eric exhibited his skill set to strangers, and it paid off. He received a one-third partnership without any financial investment. This meant Eric would perform all of the tasks needed to get the restaurant up and running while the other partners provided the finances.

During this period of Eric’s life, he saw the results of the daily goal setting and the pay-offs from hard work, determination, and learning the importance of communication and critical thinking.

Eric’s “why me” attitude transformed into “why not me?” After several years working at the New York City restaurant, Eric and his two partners decided to sell the business. Eric realized a financial gain from the sale and immediately realized he was unemployed again.

From his previous experiences, Eric had the confidence to continue moving forward with other opportunities he created independently. He developed what has turned into his life motto “If you create clarity, you’ll be confident and strong.”  In other words, if you develop small achievable goals (clarity), the only thing holding you back is your fear of failure.


While going through any serious life struggle, it may not be easy to spot opportunities for growth, whether personal or professional. However, seeing and hearing about how other people overcame their struggles may help people develop a plan for the future. With hard work and focus, opportunities may present themselves anywhere.

To be successful upon my release from prison, I knew I needed to learn different ways to speak with different people in my life. While communicating with my case managers and probation officers, I learned how to think critically. In other words, I learned not to speak to my case manager the same as I would a personal friend. These conversations also helped me expand my vocabulary while gaining confidence in my abilities.

Anyone in prison could work on these skills. People can learn from leaders like Eric through our course, or they may find people around them that have lessons to share. Participants who have concerns about life after prison may think about responses to the following questions:

  • What are you doing today to prepare for new opportunities?
  • What goals can you set for today and tomorrow?
  • In what ways will today’s goals influence tomorrow’s opportunities?
  • What can you do to find mentors in the place where you’re currently serving time?
  • What can you read to learn skills that will help you after you’re released?
  • How can you be the change that you want to see in the world?

Entreprenurial Success:

Through his initial successes, Eric found “life is what we make it.” Our character makes us each special and makes us important to other people. People should acknowledge that we all have strengths and weaknesses. If we deal with such facts of life responsibly, we build our character in ways that make us more valuable to prospective employers.

After the sale of the restaurant, Eric found himself with some capital, but again without a job. While this could create problems for some, Eric decided not to let his mind get in the way of his future success. Eric realized career paths other than college could be successful. Every day, we ruminate on questions that can prompt us to make progress:

  1. Are you feeling good about yourself?
  2. Did you do the right thing?
  3. Are you feeling healthy?
  4. Are you cultivating healthy relationships?
  5. Are you improving your language and grammar? This includes:
    1. Speaking slow enough so others can understand you;
    1. Speaking clearly;
    1. Using vocabulary your audience may know; and
    1. Being honest.

Not long after the sale of the restaurant, Eric started an equipment-leasing company. Like his prior businesses, Eric knew nothing about leasing office equipment to businesses. Unlike most people, Eric took the time to read about this business, to speak to people already in this industry, and reached out to an author of one of the books he read. Eventually, Eric met with an author, and the author became Eric’s mentor in business.

Throughout his career, Eric’s businesses have created more than 2,000 jobs for people. Eric knows that, had he cratered to his fear of failure or denial, he would not have had the success he enjoys today. Denying oneself can be a challenge for everybody. People tend to take denials and put them in a box so that we can survive (and thrive) in other areas of our lives.

We all must learn to accept who we are, and let people get to know us. Every conversation we have creates an opportunity to build a new relationship or strengthen an already existing relationship. According to Eric, “[y]our character and who you are reflective of the people you interact with.”

Eric sold his office equipment business for a profit. Once again, however, he found himself unemployed.

Shortly after he sold his second business, he started a property management business in New York City.  As with his prior endeavors, Eric knew nothing about this industry. He spoke to real estate agents and brokers and developed relationships he still has today. While his property management business started slowly in his one-bedroom apartment, it eventually managed properties worth more than $50,000,000.

In this business, Eric knew the market for his services would have many small transactions instead of one large transaction. Transactions occur when one person gives something of value to another in exchange for goods or services. Unbeknownst to many people in prison, transactions can occur with case managers and probation officers. People in prison can always exchange their positive attitude and abilities to someone else in exchange for a better outcome. Participants should strive each day to obtain positive relationships with encouraging people.

With these transactions, Eric diversified his business transactions to many other types of ventures. For instance, Eric’s business took a small percentage of the maintenance work performed at each property and in each apartment. From painting to plumbing to electrical work, every type of work paid Eric’s business a small percentage when the property owner paid the invoices. These opportunities presented themselves to Eric – not because he was lucky. Eric worked daily on his communication skills. The hard work paid off due to his persistence.

At this point, nothing should hold a person back from reaching dreams. Eric believes “the sky is the limit” if you have the passion for accomplishing goals.  There are two important lessons to take away from this lesson:

  1. The failure story running through a person’s mind is not the total sum of who you are as a person;
  2. What you do next dictates if and when you reach your goals.

Critical Thinking Questions:

  • Write at least three paragraphs, with a minimum of three sentences each, for each of the following questions.
  1. How did Eric overcome his early childhood challenges?
  2. What struggles have you encountered? Are they similar to Eric’s?
  3. What initial goals did you set in your life? How do they compare to your plans today?
  4. In what ways did Eric’s pursuit of his daily goals help him reach his eventual success?
  5. Eric refused to let his past homelessness serve as an obstacle for his future. What can you do to help prevent your time in prison from being an obstacle in your future?
  6. Eric exercised patience and perseverance in reaching his goals. In what ways might you do the same to create your new life?
  7. What elements of Eric’s past helped him succeed in running his businesses?
  8. How can you set small goals that are easily measured?
  9. Eric recognized his strength in spirit and resolve. What strengths do you have, and how can you best use them going forward?
  10. In what ways would developing more robust communication and critical thinking skills help your post-incarceration development?

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