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 Success After Prison: Trucking 

Picture of Michael Santos

Michael Santos

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Ryan teaches us about success after prison with careers in the trucking industry.

Through hard work and perseverance, Ryan started with a part-time job, earned a college degree, and started his own business. Ryan credits hard work, determination, and excellent communication skills as the keys to his success.

Our entire team at Prison Professors expresses gratitude to Ryan for sharing his experiences with us. Ryan has demonstrated how hard work, determination, and individual goal setting will lead to financial success and independence. 

Ryan’s Back Story:

Ryan grew up in a small community in Utah. Blue-collar jobs drove the local economy in his hometown. As a child, Ryan learned the value of working a full day and working hard.

Ryan earned good grades throughout his childhood, but even as he completed the necessary coursework to graduate high school, he felt dispassionate about school.

At the age of 16 and while attending high school, Ryan obtained his first job delivering and installing appliances. As an entry-level employee, he focused mainly on following instructions and working with coworkers to accomplish tasks. Over the course of four years with the company, Ryan’s employer promoted him into management roles that brought more responsibility and increased earnings. He derived great satisfaction from coaching, motivating, and encouraging others to work effectively and efficiently. He modeled the importance of doing good work and completing jobs and tasks to the best of his ability.

Ryan learned how to communicate effectively with his co-workers, superiors, and business owners. At his part-time job, Ryan delivered appliances to customers’ residences. His job duties included all the following:

  • Loading household appliances onto the delivery trucks
  • Driving the delivery truck to the customers’ home
  • Unloading the appliances from the trucks
  • Carrying the appliances into the customers’ home
  • Complete setup and cleaning, and
  • Instructing the homeowners on the proper use of the appliance.

Ryan found great satisfaction through these customer interactions. Most teenagers do not experience the opportunity to speak face-to-face with business customers. Ryan believes these interactionshelped him develop the business communication skills that helped him later in life.

The increased responsibility Ryan experienced in managing several other employees proved exciting and challenging. Ryan managed his schedule and workload as well as the schedules and workload for his employees. He held them accountable for their actions and tried to motivate them to work harder.

Ryan’s Business Development:

At the age of 21, Ryan obtained a full-time position as an assistant terminal manager with a regional trucking company. It was his first exposure to the trucking, transportation, and warehousing industry. This job provided Ryan the potential for the growth he desired and increased his earning prospects. Although Ryan viewed this job as an “entry-level” management role, his responsibilities increased from his previous delivery job. He had the responsibility of hiring dock personnel, overseeing employees who sorted products and merchandise for further transit and re-directed the products to other trucks.

Ryan defines important entry-level skills for warehouse work as personal attributes

  • Entry-level skill #1: a strong work ethic. Ryan believes that gaining upward mobility or achieving success without a strong work ethic is near impossible to. That means a person must get to work on time; show up with a positive attitude, ready to work. Great employees have a desire to get the work done, an attitude to learn, and they aspire to do good work while on the job. These foundational attributes open new opportunities.
  • Entry-level skill #2: an ability to physically do the job. A person must also efficiently and accurately operate technology such as scanner tools, and electronic tools that keep track of and relocate items through the facility.
  • Entry-level skill #3: organization is an essential aspect of any transportation and warehouse job. Items are moved and sorted for logistical reasons, which requires accuracy to move parcels from one location to secondary location to final destination.

Accuracy and attention to detail are important attributes in this industry. At this time, demand for good labor does not require a college degree. The strongest differentiators are foundational skills listed above, and the work ethic a person brings to the table.

Ryan worked as assistant manager for the transportation company for more than three years. Although he had little interest in school, he realized that education mattered in the real world. Ryan saw that communicating with clients and colleagues in the business world was especially important. Situations where people could not properly articulate their thoughts into words created difficulty for them. As assistant manager, Ryan saw how his supervisors used strong communication skills with their business customers to increase sales and drive revenue.

Ryan eventually transitioned from his full-time job to a part-time job while finishing his four-year degree in business. His commitment to his future paid off when he returned to work full time. The more skills Ryan developed, the better quality of jobs he earned. Additionally, along with Ryan’s increased level of responsibility came salary increases.

His employers responded positively to his college degree, and Ryan believes it demonstrated that he was willing to invest in himself. Although earning a college degree may take two to four years, Ryan says the delayed gratification pays dividends over the long-term. Showing the willingness to invest in yourself also allows potential employers to invest in you by offering employment.

Ryan’s growth within with the transportation company included management roles that brought increased levels of responsibility. In addition to his tasks, Ryan supervised more than 500 employees, including drivers and others who worked in administrative and management positions at the transportation company. As senior vice president, Ryan hired dozens of employees and created many jobs for his community. Eventually, three managers reported to Ryan daily. Ryan realized his hard work in developing his ability to communicate clearly and succinctly helped him in his role as senior vice president.

Through his experience as a senior vice president, Ryan also learned the importance of preparing for long-term stability as a business owner. Ryan worked for the transportation company for more than 22 years. During that time, he learned many lessons but decided to take a risk and become his boss.


During my 26 years in prison, I learned valuable lessons from leaders like Ryan. Whenever I saw a successful person who started a company, it taught me that the more we learn, the more we position ourselves for new opportunities. In prison I adopted the habit of starting my workday early. I trained myself to wake up without an alarm clock. (I still do so nearly a decade after my release.) I used that early morning time to prepare myself for the challenges I knew I would face when I came home. I cultivated a solid work ethic and discipline. I knew that sitting in jail or prison prevented me from developing managerial responsibility and experience. But I could develop and further my math and English skills, my written and communication skills. Doing so prepared me for higher levels of responsibility upon my release.

Technology did not exist when I went to prison in 1987—no internet or cell phones or email. When I left prison, I faced a steep learning curve to grasp the knowledge I’d need to build a business centered on technology. Yet, the communication skills I spent years developing inside of prison accelerated my progress when I reentered society.

Learning technology requires discipline and an ability to comprehend complex concepts. People in jails and prisons may not have access to technology, but developing skills in reading, writing and comprehension while serving time in prison advances post-release prospects for success.

Our lessons and courses offer practical tools that ease the transition from prison to society and propel you toward your highest potential. Never stop investing in yourself. While you may not currently be able to drive a truck or manage other people, if you’re viewing this video from prison you can still develop your skillset in ways that position you for higher levels of responsibility. Setting achievable goals for yourself will place you on a path for success.

From prison it may not seem so easy to spot opportunities for personal growth. By listening to stories like Ryan’s, we see the importance of self-motivation and goal setting. Sometimes opportunities present themselves where you least expect them. No matter what situation you’re faced with, you should be cognizant of the words you use and how your audience receives them. In other words, think about your choice of words and how other people will perceive them.

  • What are you doing today to look for new opportunities?
  • How can you choose better words when speaking with others?
  • Identify a fellow person in prison that can help you develop new skills.
  • How can you develop your communication skills to speak more effectively?
  • In what ways have you already improved your skillset?

Ryan believes the current computer-driven business environment provides many chances for success, provided individuals possess excellent math and communication skills. Opportunities exist if people make the best of their situation and take advantage of the available programs. Even if computers are not readily available, people can increase their chances for success by increasing their reading, writing, vocabulary, communication, and arithmetic abilities.

  • What worries do you think Ryan had when he left his part-time job after graduating high school?
  • In what ways do you think he overcame his fears?
  • How do your worries affect your life?
  • How can you position yourself to overcome negative thoughts?
  • Ryan set goals for himself in a small community. How can you set goals for yourself in your situation?
  • How did developing math and communication skills contribute to Ryan’s career growth

Ryan’s Keys to Business Success:

According to Ryan, the prevalence of technology in today’s world requires a basic understanding of computer spreadsheets that are used for tracking business operations. Most businesses require proficiency with adding and subtracting columns, and simple multiplication. Communication in business is essential. Potential customers and stakeholders expect you to articulate and converse at a level that communicates what you’re trying to accomplish, what you need, or what your business delivers. Failure to communicate effectively will quickly doom your business.

Ryan reached business success as the senior vice president of the transportation company. Despite this success, Ryan set his sights on other goals.

Ryan left his position as senior vice president and started his own trucking company in December 2019. Ryan’s trucking company started with one truck. Ryan’s company obtained the proper Utah Department of Transportation authorization in January 2020. At year-end, with one truck Ryan’s company earned $400,000 in gross revenue. Ryan says that if an individual is driven and wants growth, acquiring more trucks increases business income.

Although only now partly through 2021, Ryan estimates his company will earn $1.2 million in gross revenue in 2021. Ryan attributes this dramatic increase in revenue to his purchase of three additional trucks. Based on his experience and projections, Ryan believes each of his trucks will earn between $20,000 to $30,000 in net profit in 2021. Net profit means the amount of money the company keeps after payment of expenses (like payroll, fuel, maintenance, insurance, etc.).

As a business owner currently in the trucking industry, Ryan believes the industry has never experienced a higher demand for hard-working employees with a commercial driver’s license (CDL). The “Class A” CDL allows individuals to operate tractor-trailer trucks of up to 80,000 pounds of gross vehicle weight

According to Ryan, the trucking industry offers well-paying, full-time jobs. These jobs can pay more than $65,000 per year for 40-50 hour work weeks. Due to the current high demand, Ryan projects motivated drivers with a Class A CDL license can earn between $80,000 and $85,000 per year.

Ryan offers sage advice to someone thinking about starting a trucking business after their release from prison. Obtaining a Class A CDL is the first step. Several large trucking companies offer on-the-job training for those interested individuals who don’t know how to drive a tractor-trailer truck. In return, these companies require these employees to work for their company for a certain length of time (for example, two years after completing training). Additionally, independent truck driving schools offer educational courses for driving tractor-trailers for an upfront payment of $5,000 to $6,000. Some grant and educational programs exist that may help with financing.

The cost of a brand-new tractor with a sleeping area ranges from $150k-$165k. A heavily used tractor with an excess of one million miles ranges from $15k-$20k. Ryan recommends that someone just starting out as an owner/operator in trucking purchase a reliable used vehicle with good maintenance records and good care. A mid-range used vehicle with 500,000 miles ranges from $40k – $60k.

While the annual salaries sound enticing, Ryan believes only individuals with a willingness to work hard and show up on time will succeed. Based on his decades of experience, Ryan also emphasizes strong organizational skills and self-motivation as crucial keys to success. Lastly, Ryan looks for employees who can handle the logistical aspects of handling the customer’s merchandise with care and complete the deliveries on time.

People experiencing challenges can work hard to make a better future for themselves. By developing good work habits and creating a daily routine, they can sow the seeds for success.

Ryan’s belief that constant self-motivation and self-improvement will have long-lasting effects.

The question remains for each of us: “what can we do today to shape our future?”

Consider for a moment how lessons from Ryan’s achievements might help you advance. Ryan dedicated himself to hard work and incremental success.


Ryan is the type of person I would have listened to while I was in prison. His message would have taught me that people in jails or prisons don’t always have to be beholden to a job or an employer or answer questions about their backgrounds. If I developed a skillset, a strong work ethic, and good communication skills, I could create my own opportunities.

Ryan defined success in his life. He invested in himself with education, had a long career, and then pursued his dream of being a small business owner. He couldn’t have done that without following the steps in our program. The motivation behind Ryan’s success should inspire you to consider achieving success on your own. When people create their own job and their own business, they no longer need to be concerned with getting a job when they have a felony record.

To advance career prospects and go into business, it is crucial and essential to understand the importance of overcoming problems faced by many people in jail and prison. Learn how to master addition, subtraction, multiplication and division. Fluency with basic math positions you to learn basic digital spreadsheets (Excel and Google Sheets) and prepare for advancing career prospects after prison. Learn how to put words into sentences and sentences into paragraphs; learn how to respond with critical thinking—think, how will my vocabulary influence my customers and employees, and my business?

Ryan’s message presents people in jails and prisons with a pathway they can follow to create their own jobs. He emphasizes that “Nothing in your background would stop you from pursuing a good living for you and your family. Hang in there, dig in, do what it takes to be successful. Opportunities are waiting for you.”

Within the transportation industry, thousands of opportunities for good paying jobs exist. Applicants will not be encumbered or judged by their backgrounds, and the lack of HS diploma will not obstruct formerly incarcerated people from pursuing a career in trucking. Ryan’s final message is that virtually anyone with a good work ethic and positive attitude can be successful as a truck driver for many companies.

Ryan’s hard work differentiated him from others while finishing his college degree. Ryan saw himself as a successful businessman when he left the company he worked with for 22 years. He visualized himself as a business owner with more time to spend with his family and earning more money. Ryan took action to create success in his life. Others can follow Ryan’s path by investing in themselves and making a plan for success.

We all can learn from the lessons he offered in the interview segment that accompanies his lesson plan. Exercise patience and humility.

Critical Thinking Questions:

  • Write at least three paragraphs, with a minimum of three sentences each, for each of the following questions.
  1. How did Ryan achieve success through delayed gratification?
  2. What lessons can we take from Ryan’s dedication to long-term success?
  3. What past goals have you set in your life, and how do they compare to your plans today?
  4. Describe how you view your skillset. Are you an entrepreneur or an employee?
  5. In what ways did Ryan’s advice inspire you to make positive changes?
  6. In what ways can you create a new future for yourself after prison?
  7. How did Ryan’s experience living in a blue-collar community help him climb the corporate ladder?
  8. How can we create an environment to encourage and aid in our success?
  9. Ryan recognized his strength was hard work, grit, and determination. Have you recognized your own strengths? How can you best use them going forward?
  10. In what ways did Ryan’s communication skills aid in his professional development?

Prison Professors, an Earning Freedom company, works alongside (not in place of) civil and criminal defense counsel to help clients proactively navigate through investigations and prosecutions. Our team also helps clients prepare mitigation and compliance strategies.

If you have any questions or are uncertain about any of the issues discussed in this post, schedule a call with our risk mitigation team to receive additional guidance.

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