As we come to the end of May 2026, I am celebrating.
For the second time since completing my sentence, my liquid assets have grown by more than $1 million during a single month. I recognize that number may sound unusual coming from someone who served 26 years in federal prison. I also recognize that some people may misunderstand why I would share it.
I do not share that number to impress anyone. I share it because people in prison need to see evidence that preparation can change the trajectory of a life.
The journey has not always moved in a straight line. There have been months when the value of my liquid assets declined substantially. Those ups and downs are part of life, business, investing, and growth. The 26 years I served taught me to keep a long-term perspective. I learned not to let temporary losses define me, and not to let temporary wins distract me.
Still, when I see results such as the increase of my liquid assets by more than $1 million during a single month, I feel gratitude, humility, confidence, and a sense of responsibility. Those results did not come from one decision. They came from a plan that began decades ago, when I was still living inside federal prisons and trying to prepare for the life I wanted to build after release.
It is time to celebrate.
So how am I going to celebrate?
Not with major purchases, but with meaningful work. Tomorrow, on Monday, June 1, I’ll board a flight from Miami to New York City. From there, I’ll rent a car from Hertz and drive to Pennsylvania, where I will continue the work that gives my life purpose: going into prisons to teach people inside about the importance of preparing for success after prison. At this stage in my life, success is not about the money. It is about the impact we can make on more than 1 million people in prison, and on the families and communities waiting for them to come home.
That mission grew directly from my own experience. The decisions I made while serving my sentence had a direct relationship to the opportunities that opened after my release in August 2013.
When I went to prison in 1987, I did not know what to expect. After a judge sentenced me to 45 years, I knew that I had to change the way I thought. If I continued thinking the same way, I would continue getting the same kinds of results.
Instead of dwelling on what had happened, I had to think about what I could do to prepare for the journey ahead. Books helped me accept responsibility for the life that would follow after my release. I concluded that, after decades in prison, I would likely be unemployable. It would not make sense to complain about the obstacles I would face. My responsibility would be to prepare in ways that would help me succeed despite those obstacles.
That acceptance influenced my adjustment. I worked to earn academic credentials, contribute to society, and build a support network. By making that commitment early, I made incremental progress through prison. The strategy helped me develop tools, tactics, and resources that I could use through 9,500 days in prison.
By executing the plan, I returned to society strong, with my dignity intact, and with opportunities to prosper.
After becoming financially independent, I transitioned my career. Rather than focusing on earning more money, I began thinking more about impact. I wanted to share strategies that helped me through multiple decades in prison. That commitment led me to form Prison Professors Charitable Corporation.
Prison Professors is a non-revenue-generating nonprofit.
We provide free resources for people going through different stages of the criminal justice system.
We do not charge people in prison.
We do not charge institutions.
We do not want money to become a barrier to learning.
Our goal is to help people prepare for better outcomes.
Preparing for the World as It Exists
Many well-intentioned reentry programs focus on encouragement, emotional support, and awareness of the barriers people face after prison. Those barriers are real. A criminal conviction can make it harder to find employment, housing, credit, trust, and opportunity.
People with criminal records often face closed doors, skeptical employers, and systems that do not always reward personal growth.
At Prison Professors, we acknowledge those barriers, but we do not think it is helpful to award participation trophies or celebrate program completion unless that preparation leads to stronger records, better decisions, and measurable progress. If a person goes through a program but finds the market unresponsive after release, what’s the point? We should not celebrate the process alone. As many people who leave prison discover, the market doesn’t care about the process. We should celebrate preparation that leads to stronger records, better decisions, and measurable results.
We teach people to prepare for the world as it exists. Complaining about the challenges of a criminal record may describe the problem, but complaints alone will not create better outcomes. To improve outcomes, people need strategies. They need discipline. They need documentation. They need a record that shows how they used their time.
The hard reality is that people leaving prison often face one of several outcomes. They may become:
Unemployed,
Underemployed,
Homeless,
Arrested again, or
Successful.
Every day, a person with a criminal record makes choices that influence which of those outcomes becomes more likely.
That does not mean every obstacle is fair. It does not mean every person starts from the same place. It does not mean preparation guarantees success. But preparation improves prospects. It gives a person a stronger record. It creates evidence that a person can use to self-advocate, so that others will see more than the conviction.
At Prison Professors, we want people to connect the dots between the decisions they make today and the opportunities they may create tomorrow.
Focus on Results
LinkedIn and other platforms are filled with articles about the difficulties of reentry. Many of those articles describe how hard and unfair it can be to find employment, housing, credit, trust, and opportunity after a conviction. Those challenges get a lot of attention.
But people in prison also need more than awareness of the problem. They need a path.
At Prison Professors, we do not encourage people to pursue participation trophies. The world does not reward people simply because they say they have changed. Decision-makers want results. Employers, probation officers, case managers, judges, creditors, landlords, and community leaders want to know what a person has done to become more trustworthy, more skilled, and more prepared.
And talking only about how unfair the world is does not inspire confidence. The self-directed lessons from Prison Professors urge people to anticipate problems and prepare solutions. They advance prospects for success when their plans anticipate obstacles. They build skills, document progress, and position themselves to seize or create opportunities.
That is why we encourage people to memorialize the steps they take to prepare for success. We offer free books and courses to prompt self-directed learning. We encourage people to write biographies, keep journals, complete book reports, develop release plans, and build records that show growth over time.
Those records lead to better results.
A person may say he wants a job. A documented record can show that he has been preparing for employment.
A person may say he values education. A documented record can show what he has studied and how he has applied what he learned.
A person may say he has changed. A documented record can show the decisions, reflections, and actions that support that claim.
We want members of our community to become the CEOs of their lives. That means they identify problems, define solutions, build tools, measure progress, adjust when necessary, and execute their plans.
The real world does not offer second chances simply because a person wants one. Opportunities are more likely to open for people who prepare. That preparation requires discipline, documentation, and a willingness to work on oneself long before the opportunity appears.
Today's Decisions: Tomorrow’s Opportunities
When I speak with people in prison, I emphasize the importance of documenting the journey. Success comes to those who sow seeds before harvest season.
To the extent that people develop release plans, write biographies that show they are more than the crime, journal in ways that demonstrate a commitment to self-directed learning, and record what they learn from the books they read, they advance their prospects for better outcomes.
It is never too early to start.
It is also never too late to start.
But each person should be honest about the decisions he is making. He should think about the realities of the world and assess his level of commitment to prepare. No one can fake preparation for success. We do not help anyone by pretending that participation alone is enough.
People want results.
That is what differentiates Prison Professors. We do not sell hope as a feeling. We teach preparation as a strategy. We encourage people to build a record that can lead to better outcomes.
Living as the CEO of Your Life
Someone once asked me what makes Prison Professors different from other nonprofits that focus on reentry.
My answer is simple: if a person works through the free courses that Prison Professors offers, he is learning how to live as the CEO of his life.
What does that mean?
It means he identifies the problem. The world is not always kind to people who have a criminal background.
It means he defines a solution. He identifies what success should look like, then engineers a plan that will advance his candidacy for that success.
It means he builds tools, tactics, and resources. If he participates in Prison Professors, he works through free courses and documents the steps he is taking to prepare for success.
It means he adjusts when necessary. When the environment changes, he shows how he pivoted, adapted, and continued moving forward.
It means he executes the plan. Every day, he advances in a deliberate way, putting himself on the pathway for the next opportunity.
Those lessons empowered me through the 26 years that I served. I would like to say I came up with them on my own, but that would not be accurate. I learned from leaders, CEOs, authors, entrepreneurs, people who achieved extraordinary success, and from the teachings of Jesus.
All of those sources reinforced a simple lesson:
The harder we work on ourselves, the more we advance our prospects for success.
Invest in Yourself First
Some people may want to know how my liquid assets grew by more than $1 million in a single month. I will write about the investments I make elsewhere, because I do not want anyone to misconstrue what I do with financial advice. I am not licensed or qualified to offer financial advice to anyone.
The lesson here is not about copying my investments. The lesson is about learning how to think differently.
While I served my sentence, I believed the best investment I could make would be to invest in myself. If I learned how to think differently, I could improve my chances of overcoming the obstacles presented by prison and by the criminal conviction that would follow me after release.
It was never my goal to be a model inmate. My goal was to become successful after prison. To do that, I needed to engineer a plan.
Regardless of what the system did, or where it held me, I could always work to develop skills that would help me create value.
Those skills included:
Communication Skills: By learning how to read better, write more persuasively, and express ideas clearly, I could open more opportunities, regardless of where authorities confined me.
Critical Thinking Skills: Through self-directed learning, I could become more skilled at making decisions, solving problems, and using limited resources in ways that created value.
Understanding Markets: By learning how markets valued different asset classes, businesses, and opportunities, I could strengthen my prospects for higher earning potential after release.
For that reason, I encourage people in prison to understand that before they invest in markets, businesses, real estate, or any other asset class, they should invest in themselves. They should become better communicators, better critical thinkers, and better students of how the world works.
A good investment in skill development can lead to more opportunities. If those opportunities are executed well, they may lead to prosperity, freedom, and a stronger ability to contribute.
That is the message I will carry into prison this week.
I am grateful for the progress in my own life, but I am more grateful for the opportunity to use that progress as a teaching tool. Every person in prison should know that today’s decisions influence tomorrow’s possibilities. The sooner we begin preparing, the more we can build lives of meaning, contribution, and success.
Self-Directed Questions
What decision can I make today that will improve my prospects for success after prison?
What evidence am I building to show that I am becoming more trustworthy, skilled, and prepared?
How can I use writing—through a biography, journal, book report, or release plan—to document my growth?
What obstacle am I likely to face after release, and what solution can I begin preparing now?
Am I celebrating participation, or am I building a record that can lead to measurable results?