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 12-Success after Prison 

Picture of Michael Santos

Michael Santos

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To reach our goals, we need many resources. The relationships we build today can lead us closer to those resources, both financial resources and human resources.

Chapter 12: Raising Capital

I’m grateful to Plato, the philosopher who lived longer than 2,000 years ago and wrote the story of Socrates. His teachings influenced my thinking and approach to solving problems.

I relied upon a Socratic, question-based approach to learning to figure out the next steps in my career development. The more questions I asked, the more truth I found in the saying:

  • The one thing I know is that there is a lot that I don’t know.

By spring 2014, I’d been free from the Bureau of Prisons for eight months. By then, I had nearly finished teaching the second semester at San Francisco State University, and I’d become more familiar with the different technology applications, hardware, and software. 

Social media helped to spread awareness for the work I was doing, and that awareness opened opportunities. Still, I would need resources to fund airfare, lodging, and local transportation as I traveled to meet with administrators who might consider offering the Straight-A Guide in their institutions.

I crafted a plan, hoping to find ten corporate sponsors who would pledge $10,000 annually for three years. With $100,000 in annual sponsorship, I hoped to work full-time toward creating and distributing courses that would improve outcomes for people in America’s criminal justice system.

Newport Beach:

In my search for corporate sponsorship, I called Andris in the spring of 2013. I met Andris during my final months at the Atwater prison camp. He served a brief sentence for a white-collar crime, and I enjoyed listening to him describe the different businesses he launched before authorities charged him with obstruction of justice.

During his senior year in college, Andris launched Ameridebt, which he described as a debt-consolidation business. As a fee-based service, the business helped consumers renegotiate their debt with credit-card companies—Andris leveraged profits from that venture to launch numerous other ventures.

Andris served time in the federal prison camp at Atwater as an indirect result of a civil investigation. The Federal Trade Commission had sued Andris and the company he founded for deceptive advertising. His settlement agreement with the agency required Andris to cooperate fully with the agency. When he refused, prosecutors brought an obstruction charge. Rather than fighting the case, Andris pleaded guilty, and a federal judge sentenced him to a term that would require him to spend nine months in the Atwater federal prison. Despite that setback, Andris remained optimistic because of a separate property development company that he owned. Based out of Newport Beach, the business generated more than $20 million in annual revenues.

When I called Andris and requested that his business sponsor my efforts, he invited me to visit him in Newport Beach. Since my probation officer had authorized me to travel domestically and to meet with anyone to develop the venture I intended to build, I agreed to book a flight from San Francisco to Orange County. When we met, I told Andris about my ambitions of creating products and services that would improve the outcomes of America’s criminal justice system. He listened patiently, and then he asked me a series of questions:

  • “Why would people who operate prisons care whether people inside came out successfully?”
  • “What makes you think administrators would buy products you create?”
  • “How long would it take before you start generating purchase orders?”
  • “Can you build a business around these ideas?”

His questions prompted a lengthy discussion. From Andris’s perspective, people didn’t care about the prison system or the people serving time. I felt it was my job to change those perceptions. Wanting more people to realize that our nation’s commitment to mass incarceration influenced every American citizen, I asked for his help.

“I guess you need to ask yourself a question,” he said. “Do you want to change the world, or do you want to make money?”

I thought I could succeed on both fronts, earning a good living while working to empower and inspire others.

“Maybe you can, maybe you can’t,” he responded. “But you’ve got a lot of passion for this stuff that no one cares about. If you could translate some of that energy into business, you could come work with me, start making money right now, and build products to change the prison system on the side.”

I asked what he had in mind. Andris invited me to join his team as a full-time employee and contribute as needed. Showing he wasn’t a guy who made empty offers, he pledged to cover my housing expense for the first year and pay a $100,000 salary while we figured out what I’d do.

What’s the lesson here?

Some might say I was lucky. In my view, we create our luck. Had I not sown seeds early during my prison term, Andris would not have believed in me. He wouldn’t invest in a person unless that person made a massive investment in “self” first.

  • What investment are you making in yourself today?
  • What investment can you make in yourself right now that will influence other people to invest in your future?

Transferring Jurisdictions:

Since I hadn’t completed my term of Supervised Release when Andris offered the job, moving from San Francisco to Newport Beach would not be easy. Authorities required that I report to a probation officer in the Northern Judicial District of California. Employment with Andris’ company would require me to relocate to Orange County and transfer my probation to the Central Judicial District of California. 

Besides convincing my probation officer to support my move, I’d have to persuade a probation officer from the Central District to authorize my transfer. 

If I could overcome those challenges, I’d have a few additional complications to resolve. Fortunately, the seeds I began sowing at the start of my journey positioned me to seize opportunities like the one Andris offered. 

Carole liked the idea of transitioning from working exclusively for the prison industry and pursuing other ventures. The compelling job offer would open new opportunities. 

I took the next step of contacting my probation officer. Once the probation officer assured me he would support the move, I told the university that I would not return to teach at SFSU in the fall of 2014. Instead, Carole and I would move to Southern California.

Return on Investment

A conventional mortgage company gave Carole and me the financing we needed to pay for the house my friends Lee, Seth, and Chris allowed us to purchase. Since acquiring the property in 2012, when I first reported to the halfway house, the housing market in the San Francisco Bay area has skyrocketed. We could’ve sold the house quickly for a substantial profit.

Feeling that housing prices would continue to rise, Carole and I agreed to hold on to the property. We would find suitable tenants who would rent from us. The rental income we received would allow us to pay the mortgage and keep the property as part of our retirement plan. If all went according to our plan, Carole and I would own the property outright by the time we turned 65. By then, we anticipated the house would be worth more than $1 million. We considered the investment an excellent resource to advance our goals for a stable retirement.

Owning real estate, it would seem, could become an integral component of our plan to build a million-dollar net worth within five years. Carole and I pledged to work together in ways that would position us to acquire more.

Orange County:

After teaching my final class at SFSU in May of 2014, Carole and I loaded our small, four-cylinder Chevy for the seven-hour drive from San Francisco south to Newport Beach. 

Despite our income and accumulated savings, Carole and I lived frugally and didn’t splurge on purchases that would likely drop in value—like a luxurious automobile. All our daily decisions come with opportunity costs. Leaders would lose respect for my judgment if I were to splurge on an expensive car before building financial security. I needed to make prudent decisions to generate the support that helped my adjustment.

Both Carole and I pursued long-term stability, and we both worked toward those goals each day. When we left the San Francisco Bay area, we had about $100,000 equity in our house and another $100,000 in savings. We considered ourselves fortunate because my 26-year prison term had ended only ten months previously.

We arrived in Orange County just in time to celebrate Mother’s Day with my mom and Grandma.

Digital Businesses:

Andris employed more than 100 people, and I hardly interacted with any of them. He employed marketing people, technology people, and an entire floor of salespeople. They asked me for assistance with writing or editing, but other than that, they left me alone. I had the autonomy to develop new business ideas, which led me to form the business that built our website, branded Prison Professors.

Although prison provided the context of my story, my message centered on overcoming struggles. That message had broad applications. Every individual experiences struggle. Too frequently, those struggles derail an individual’s confidence. People who experienced challenges that included financial reversals, divorce, obesity, business, or career complications, lived with misery. If we could create products and services in a digital format, we could build something that scaled.

I considered Andris more of a friend and mentor than an employer.

I used my time in the office to learn how to create resources that would allow me to deliver the message in any format that consumers would want, either text, video, or audio.

To paraphrase the celebrated professional hockey player Wayne Gretzky, I needed to skate to where the puck was going rather than to the puck. From my perspective, the educational market would expand. We could produce digital products less expensively, making them easier to distribute.

I intended to create content that would apply to every citizen who aspired to overcome struggle and reach a higher potential. I’d need to build in stages:

  • I’d need to create an abundance of content that would be freely available.
  • I’d need to create proprietary content that I could sell.
  • I’d need to ensure that anyone who had access to the content would find a powerful and actionable message of personal development.

With a plan in place, I started scouring the internet to learn more about how to create digital products.


Research led me to a webinar on podcasting. The platform could allow me to communicate with people through audio—as if I had a private radio station. Anyone with an internet connection would be able to access the recordings.

I needed to understand more about technology platforms, software, and hardware to launch a practical podcast. Rather than diving in blindly, which would likely require hundreds of hours, I spent $2,500 to enroll in a course on podcasting. Through the self-directed course, I learned everything I needed to launch the Prison Professors podcast on iTunes.

The podcast would become a part of my overall strategy to broaden my audience, letting the world know more about the courses I would create. I set a goal of creating new content for an ongoing show that would follow a coherent structure. Each episode would last roughly 20 minutes and adhere to one of three formats:

  • I would share strategies I learned from masterminds who taught me how to overcome struggle.
  • I would interview formerly incarcerated individuals who emerged successfully, and they would discuss how their adjustments inside contributed to their successful transition into society.
  • I would interview business and community leaders, asking them about strategies they used to build successful organizations—and also asking them to offer guidance for people who lived in challenging predicaments. What steps could they take to transition into lives of relevance, meaning, and contribution?

Creating a business around digital products remained the focus, and I intended to use the podcast as an integral component of the strategy.

By the end of 2015, I had recorded more than 200 episodes featuring guests from every sector of society. Several guests described their transformation while in prison. They spoke about how their adjustment patterns led to incredible opportunities upon release. Some guests talked about going to prison with histories of violence and substance abuse. Their transformation inside led to their becoming college graduates. The show featured formerly incarcerated individuals who emerged to become practicing lawyers, authors, and entrepreneurs. The podcast also featured interviews with high-profile community leaders.

Each guest shared the trait of personal leadership. They helped me communicate that it’s never too early and never too late to begin sowing seeds for a better life. Their stories show that if we choose to live in the world as it exists rather than as we wish it would be, we can create pathways that lead us to success. That strategy of deliberateness worked for the many formerly incarcerated people I feature on the podcast.

I’m convinced a strategy of deliberateness will work for anyone who chooses to lead a values-based, goal-oriented life.

Self-Directed Questions:

  • What investment are you making in yourself today?
  • What investment can you make in yourself right now that will influence other people to invest in your future?
  • How would investing thousands of dollars in personal-development courses influence prospects for success?

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