Leadership with Bill McGlashan 

Need Answers to Your Questions?

We can learn a great deal about leadership with Bill McGlashan. This multi-part course will help people in jails and prisons pursue self-directed learning.

My name is Michael Santos. I’m the founder of Earning Freedom and the Prison Professors nonprofit. If you’re working through our course, it’s likely that you’re going through the criminal justice system at some stage—pretrial, in custody, or on some form of community supervision.

Both Bill McGlashan and I can empathize with your plight.

For 9,500 days—26 full years—I lived as federal prisoner number 16377-004. I am intimately familiar with challenges of living in confinement. Despite those challenges, I know the opportunities that open when a person chooses deliberate adjustment strategies. Incidentally, when I write “deliberate adjustment strategy,” I mean that a person adjusts without expectations or excuses. If a person pursues a self-directed, deliberate adjustment, that person will not accept the myths that so many other people in prison perpetuate, such as:

  • The best way to serve time is to forget about the world outside and focus on time inside, or
  • A person in prison should only interact with people of his or her own race or ethnicity, or
  • The prison system doesn’t offer any opportunities for a person to grow, learn, or prepare for success.

When a person pursues a self-directed, deliberate adjustment strategy, that person will work towards success regardless of the external influences. The person knows that it’s never too early, and it’s never too late to begin preparing for a better life.

I learned these lessons from leaders like Bill McGlashan.

A jail or prison may or may not offer rehabilitative courses. When a person develops a self-directed work ethic, the person strives to improve for inherent reasons, and not for rewards or accolades from the system. Regardless of where administrators confine a person, that individual can develop a mindset of success.

At Prison Professors, we develop courses to help people who want to help themselves.

For that reason, it pleases me to offer another supplemental course:

  • Lessons on Leadership: With Bill McGlashan
Bill McGlashan with Bono

Some may wonder why a person like Bill McGlashan would work with a startup like Prison Professors. Bill is known across the globe as one of the foremost impact investors. Why would such a man volunteer so much of his personal time to help people locked in America’s jails and prisons?

In full transparency, my interactions with Bill began just before he surrendered to serve a 90-day sentence in federal prison. During our initial conversation, Bill expressed remorse about the crime he committed. From my perspective, his imprisonment represented a gross misuse of our nation’s resources, an outgrowth of a misguided pursuit of mass incarceration.

Yet Bill refused to allow me to minimize his culpability. He expressed disappointment in himself for using bad judgment, and for making a bad decision. Whether a law made his decision criminal or not, he knew that he had done something wrong and unfair. He wanted to make amends to the many people hurt by his decision. For those reasons, we began working together, as I’ll describe below. 

Some background context may help. Through context, participants may grasp why I feel so strongly that people in jail and prison can use this course as a resource in their self-directed adjustment strategy.


I made bad decisions as a young man, refusing to heed the advice of teachers or mentors. Excitement of a fast crowd lured me away from productive habits. I began making bad decisions during the recklessness of youth. Those decisions turned worse in 1984, when I was just 20 years old. I began participating with a group that sold cocaine. Approximately eighteen months later, in August of 1987, federal agents arrested me. I was 23. For the next 30 years, I lived inside prisons of every security level, or I served time on some form of community confinement, including:

  • High-security US penitentiaries
  • Medium-security federal correctional institutions
  • Low-security federal correctional institutions
  • Minimum-security federal prison camps
  • A halfway house
  • Home confinement
  • Supervised Release
  • Special Parole
  • Parole

As I reveal in my book, Earning Freedom: Conquering a 45-Year Prison Term, leaders taught me many lessons during that lengthy odyssey. I sense a responsibility to pass along the lessons that transformed my life, with the hopes of helping as many people as possible transform their life as well.

Even though a person may serve a lengthy term, any of us can choose to work toward reconciling with society. While in prison, I learned from many leaders. People like Bill McGlashan taught me to follow the principles of leadership listed below:

  • Define success, as the best possible outcome.
  • Create a plan and prepare to overcome the challenges ahead.
  • Put priorities in place, knowing that incremental progress, with a step-by-step approach, would lead to new opportunities.
  • Create tools, tactics, and resources that would help me grow, and
  • Execute the plan every day.

As described earlier, I’m convinced that a disciplined adjustment strategy could help any person wanting to prepare for a life of meaning, relevance, and dignity. It can help a person restore confidence. Regardless of what bad decisions we made in the past, at any time, regardless of where we are, we can work toward making better decisions.

I aspired to reconcile with society. As a person that broke the law, I violated the trust of my fellow citizens. My indictment read: “The United States of America -v- Michael Santos.” From the government’s perspective, by breaking the law, I hurt every citizen. To make amends, I would need to redeem my crimes with good works. I would need to prepare in ways that would allow me to emerge successfully, as a law-abiding, contributing citizen.

That perspective helped me to accept that I wasn’t entitled to a second chance. I would need to create my own “second chance” by atoning for the bad decisions of my youth. Leaders opened my eyes to a new philosophy. Rather than complaining about the challenges wrought by my bad decisions, I could work to make amends.

Any person can do the same.

In Earning Freedom: Conquering a 45-Year Prison Term, I share the entire story. On August 11, 1987, authorities arrested me. After a jury convicted me, a judge sentenced me to serve a 45-year sentence. While locked in jail, a correctional officer passed me a copy of Plato’s book, The Republic, which introduced me to philosophy. I learned about Socrates and his remarkable way of looking at the world.

Reading The Republic changed my life. It helped me to realize and accept the colossal mistakes I had made as a young man. I’d been living by a bad philosophy. Rather than working to help my community, I broke the law.

Socrates (and other leaders) taught me to stop feeling sorry for myself. Leaders suggested that we can change if we don’t like our situation, or if we’re facing a challenge. To start, we must change the way we think. From leaders like Socrates (and Bill McGlashan), I learned the power that comes when we think about other people and our community instead of only thinking about the challenges we face.

  • We can recalibrate.
  • We can work to earn freedom.

That change in thinking influenced a deliberate adjustment strategy. While incarcerated, I made a 100% commitment to:

  • Pursue self-directed learning,
  • Contribute to society in meaningful, measurable ways, and
  • Work toward building a strong support network that would include positive role models.

That three-pronged strategy made all the difference. When defining success at that stage in my life, I simply wanted to leave prison with my dignity intact. I wanted to pursue a path that would open opportunities to live as a law-abiding, contributing citizen. By preparing well, no one would know that I had served a quarter-century when I got out. I wanted to emerge unscathed.

That strategy led to my earning a bachelor’s degree from Mercer University, a master’s degree from Hofstra University, getting married in prison, and opening many income opportunities that I could expand upon after release. By the time I walked out of prison, I had sufficient savings in the bank to launch my career. None of that would have been possible had I not opened my mind, and my heart, to learn from leaders.

Any person that served time alongside me could have done the same. Several people volunteered thousands of hours to help me put this program together. We share a unified goal of helping others find their way to a law-abiding, contributing life upon release from prison. At any time, we can choose to learn from leaders like Bill McGlashan. Lessons from leaders can change the trajectory of our life.

Sadly, the prison culture conditions people to learn from so-called “shot callers” instead of the real leaders in the world.

Bill McGlashan Leadership

TThe leaders I studied taught me to think differently from the way I thought before I went to prison. I encourage all people in jails and prisons to do the same. Those who choose to pursue self-directed adjustments will find opportunities rather than challenges awaiting them upon release—as I experienced.

While still in the halfway house, San Francisco State University hired me to teach as an adjunct professor. While still in the halfway house, San Francisco State University hired me to teach as an adjunct professor. Simultaneously, I began building businesses. Together with my partners, we persuaded prison administrators, federal judges, probation officers, and even U.S. Attorneys to purchase our products and services. A successful adjustment inside eased my reentry, allowing me to begin building a career upon release.

Some employers have a policy of not hiring people that have a criminal history. For that reason, every person in jail and prison should understand the importance of preparing. A disciplined and deliberate adjustment strategy can put a person in a position to open income opportunities after a release from prison.

As Bill teaches us in this course, success does not come by accident.

I am convinced that any person in jail or prison can use the time inside to recalibrate and open opportunities. To succeed, however, those people must accept the reality. As administrators used to tell me:

“We don’t care anything about your life after your release. We only care about the security of the institution.”

In such an environment, we should expect obstacles. Despite obstacles that contribute to intergenerational cycles of recidivism, we must focus on what we can do to prepare for the journey ahead.

We created this course as a starting point. We must reject the dubious advice we receive:

From the system: You’ve got nothin’ comin’. Don’t do the crime if you can’t do the time.

From misguided people inside: The best way to serve time is to forget about the world outside, and to focus on your reputation in prison.

Mahatma Gandhi taught us that we should strive to live as the change we want to see in the world. I want to live in a world where people can always work to become better and reach their highest potential. I’m grateful to the many leaders who taught me this message. For that reason, I’ve devoted my professional career to sharing what I’ve learned from leaders.  

It pleases me to share these lessons from Bill McGlashan, a genuine world-class leader.

Bill McGlashan:

What qualifies Bill as a world-class leader?

A lot!

Bill has impeccable academic credentials, with an undergraduate degree from Yale, and a graduate degree in business from Stanford, two of the top schools in our country. While I served decades in prison, Bill distinguished himself as:

  • a steward of capital for private equity companies,
  • a business leader, and
  • an impact investor.

He launched startups that he later sold to publicly traded corporations. As a CEO, he saved hundreds of jobs by accepting the responsibility of restructuring a publicly traded company that was on the verge of failure. As a director of TPG Capital, he created stellar returns on more than $12 billion worth of funds that investors entrusted to him and his team.

If Bill’s titles and accomplishments don’t mean anything to participants at the start of the course, they will make more sense at the course’s conclusion. In short, people of influence considered Bill the “big boss,” the man who could make or break an idea. He was a connector of people and money at the highest level. Through his work, he built coalitions to solve huge global challenges like climate change, extreme poverty, access to healthcare and education.

Bill built a reputation as one of the world’s most successful impact investors. He brought coalitions of other world-class activists, philanthropists, and leaders together, including:

  • Bono: Singer for U2, but also founder of RED, ONE, and a cultural leader.
  • Jeff Skoll: Founder of eBay, Participant Media, and the Skoll Foundation.
  • Laurene Powell Jobs, philanthropist, and founder of the Emerson Collective.
  • Mo Ibrahim, founder of Celtel and global philanthropist focused on Africa.
  • Richard Branson, founder of Virgin Group.
  • Anand Mahindra, Chairman of Mahindra Group from India.

I did not meet Bill until the summer of 2021, eight years after I had finished my obligation to the Bureau of Prisons.

Bill acknowledges that he made a catastrophic decision as a parent. As he described in the video interviews that accompany this course, Bill knowingly paid someone to influence test scores for his son.

Bill’s decision led to a series of catastrophic events, proving the theorem of Scottish author Sir Walter Scott, who wrote:

  • Oh, what a tangled web we weave, when first we practice to deceive.

Authorities arrested Bill, a grand jury indicted him, and he pleaded guilty to a federal crime.

As mentioned at the start of this Forward, Bill and I spoke for the first time a few days before he would surrender to serve a three-month sentence in federal prison.

During our lengthy conversation, I listened to Bill express his remorse and admired his eagerness to make amends. When he told me that he wanted to use his time inside to help as many people as possible, I offered some observations on what he could expect from the experience. People in jail or prison could learn from his lessons on leadership.

Bill’s story was the type that would have inspired me to want to learn more while I served my sentence. It was the type of story to influence the books I read, or the self-study courses I pursued.

Knowing that others could benefit from his wisdom, I invited him to volunteer his time to create a new course with Prison Professors. Through the course, I suggested, we could help people learn the importance of pursuing self-directed learning projects. Since the prison system may not always have resources to offer educational courses, I explained, we could fill the gap.

As evidenced by the video files that accompany this course, and the personal nature of the lessons, Bill volunteered to spend hundreds of hours working alongside me. Together, we developed the course.

This course offers opportunities for self-directed participants to work toward developing their vocabulary, their writing skills, and their critical-thinking skills. These three building blocks can help anyone grow and become a leader. By challenging myself to develop those skills when I was in prison, I was able to open countless opportunities as the months I served turned into years, and the years turned into decades.

Bill’s teachings would have inspired me while I served my sentence. They inspire me now. They make me want to learn more. We hope they do the same for you and that you will learn from the video files, the audio files and the lessons that make up our course.

Although I didn’t appreciate the importance of education when I started the journey, this course would have opened my eyes to the liberty that comes with self-directed learning plans. On behalf of our entire team at Prison Professors, Bill and I encourage all participants to work toward reaching their highest potential.


Michael Santos

Need Answers to Your Questions?

We Have Updated Our Terms And Conditions

We have updated our Privacy Policy, Terms of Use, and Terms of Service page. To review the latest version, please click on Terms of Use. If at any time you choose not to accept these terms, please do not use this site.