Born and raised in Washington, DC, Chris Wilson grew up under extremely difficult circumstances: poverty, drug addiction, and gun violence was the everyday norm in his community. At the age of 17, he was charged with a crime, convicted, and sentenced to natural life in prison. It was during times of isolation that he decided to not only turn his life around but to make a difference in the life of people who currently live in poverty-stricken communities, similar to his childhood surroundings.

Many years ago he was quoted saying “I committed my life to self-improvement and helping others. I sat in a dark cell and wrote up what I now call my Master Plan. A plan to build a business empire and help others”. While imprisoned, Chris earned his High School diploma, graduated from all vocational shops, earned an Associate of Arts Degree in Sociology, from Anne Arundel Community College, and taught himself to speak and write in several foreign languages. He became a mentor, started a career center, book club and after serving 16 years in prison, he has returned to society as a changed man. Chris is one of those people who I have met over the last few months and really built a strong relationship with and really could say great things about. I hope you enjoy this episode.


  1. In life, there’s always going to be external and internal challenges, presenting endless competition and competitors — including yourself. You have to train your mind to embrace adversity and competition.
  2. The limit does not exist. We all encounter limits that have been placed on our path. What’s important to remember is that looking beyond the ceiling over your situation will move you forward and provide innovation and opportunity.
  3. Education is the foundation for everything. In whichever form you believe education to come in (books, school, experience, travel …), pursue it fervently; it will expand your horizon quicker and more carefully than anything else.


BRYAN WISH: What is the One Away moment you want to talk about today?

CHRIS WILSON: My One Away moment will probably have to be when I was going to the University of Baltimore and I was majoring in Community Studies and Economic Engagement. I wasn’t too excited about what I was learning because I was already working in that sector doing community organizing and writing grants. I was a bit bored with my schoolwork and I was paying for it. I was taking an entrepreneurship class and I had this really interesting professor and he was like a mad scientist in a good way in the business industry. He’d done a lot of interesting stuff all his life.

I remember after the class telling him how much I enjoyed his class but I was thinking of dropping out of school. I wanted to get out and just do it or I wanted to go somewhere else. He smiled at me and he said, “What if I told you I was working on a special program for an elite group of entrepreneurs? It’s a mixture of, like, Harvard and Oxford and we study cases and there’s a dress code and you have to generate revenue. You have to start a company. If you couldn’t do these things, then you didn’t graduate.”

I remember smiling and I was grandfathered into this very strenuous program and it really pushed me to be a real serious entrepreneur.

That was a point in my life where it really took me to the next level. I started making money, generating revenue. We’d troubleshoot and talk about war stories that entrepreneurs went through in the past and we studied the cases. I learned a lot in a short period. It was about a two-year program.  

BRYAN WISH: What was the program like? Why was this such a turning point in your life? 

CHRIS WILSON: We had to study some portions of David and Goliath by Malcolm Gladwell. It solidified the idea that successful entrepreneurs or just anyone, but especially in business, understand there’s always going to be a giant coming over that hill. To translate, that means there’s always going to be a problem that you have to troubleshoot. Some people may think you put a system in place or a company in place and you just move forward. In real life, there’s always going to be challenging, always going to be internal stuff, always going to be competition and competitors. You have to train your mind to embrace adversity and competition.

It just makes you better. That was one of the things I learned in the class and it really pushed me for when things go wrong or account receivables from city governments that we can’t pay on time and you have to figure out how to keep the time alive. What I learned in the program is that it’s Murphy’s Law. Whatever can go wrong, will go wrong, and you should be ready to deal with whatever happens. 

BRYAN WISH: There’s always going to be people coming over your shoulders and trying to take you down or over. Being cognizant and aware of that and to go through a program that equipped you for the real world was instrumental. It sounds like what more education systems should be like. Tell me more about the professor. 

CHRIS WILSON: I say this in a very respectful and loving way. He was very odd. You could say he has been a nerd all of his life. He did all these science projects when he was young and he was probably the first venture capitalist firm that set up in Russia after the fall of the Soviet Union and he kind of predicted it and planned for it and saved his money. He moved his family over. Everyone thought he was crazy. He did all this amazing stuff business-wise. Incredible entrepreneurial stories of having his shipping freight being seized by Russian generals and negotiating his way out of that stuff. All kinds of spectacular stuff.

I appreciated his teaching style. Oftentimes, he would lock the classroom door and he would chew our asses out if people weren’t taking it seriously. You weren’t allowed to be on your phone or doodling. Everyone had to get up and present and you had to know what you were talking about or he’d tell you to sit your ass down. People who showed up in his class or made it in the program, they were there to win. They were there to be successful. 90% of us. It gave us a very rich, real, school/business experience. I actually left that program and I started making serious money and never looked back. I quit my job and I was on the rocket ship. 

BRYAN WISH: What did you do after the program? 

CHRIS WILSON: My first company was a furniture design and restoration company where I took antique furniture and restored it or I did high-end build-outs in restaurants, lounges, or inside yachts. I started making money while I was in the program and my professor, before I found my first follow or proof of concept, he told me, which is strange now when I think about it, “Chris, I want you to think about your business or your service as a virus.” I was like, “What are you talking about?” He said, “You want to go out and you want to get the right people sick with your product or your service.” He was like, “Just think about that.”

My first job was in this lounge that I read that I knew that Cal Ripken, the baseball player, and his family would hang out there all the time. I said, “If I could do a really good job with this lounge that he likes to hang out, then he’ll probably tell all his friends and I’ll get some high-end clients.” That’s how I pulled it off. I got the right person sick. It’s like finding your champion. That was my strategy.

Then I came to D.C. and I started doing work for the founder of Duke Ellington School of Arts and I redid her place and a bunch of furniture. She’s friends with Oprah. It never stopped after that. I also had incorporated my company as a social enterprise. I was hiring mostly people that were returning home from prison or people who really needed help the most. I was frustrated because I wasn’t able to hire too many people because of the structure of the business and so, I started another company, a construction contracting company.

I had all these relationships with developers and we were doing demolition and we were building outhouses. I grew to 23 employees in six months. I started doing that work all over and down the east coast. We went on to win an award in the state of Maryland including a Presidential Award from President Obama. It was an interesting, good time. 

BRYAN WISH: What would you say are some of the things you learned about yourself, people, business, and the process you really felt allowed you to set the foundation in place that you’ve been able to build off with tons of art?

CHRIS WILSON: We all should create our personal board of advisors. You know when you think, in general, the standard structure of you start a company and who sits on your board? Oftentimes, the people who you want are busy. They’re not going to agree to be on your board. They’re going to be resistant. What’s the time commitment and all that? I always tell people that you trick them. You take five people who are experts in particular areas. In my case, it was someone good in finance, someone good with law, someone good with relationships, and it became my personal board.

I would have coffee or lunch or something with each one of them once a month. We’d talk about whatever issues we like to talk about. Just having that unofficial board. Some people are on my board and they don’t even know it. You could be on my board. It went both ways. I would try to contribute to their life and what was going on. I also wanted to pick their brain and get advice whether it was getting my books and my finances or navigating a relationship. This support system allowed me to handle obstacles or challenges or also see opportunities going forward in my life and in business. It was awesome and I still do it. 

BRYAN WISH: What you said is paramount. They didn’t even know they were on your personal board of advisors. It wasn’t just a take, take, take relationship. You identified people at different points of the path and you said, “Oh, I need this advice from this person. How can I go find them?” And you did it. You created value in return. How did you absorb knowledge at this time beyond people? 

CHRIS WILSON: I started eight years ago utilizing the internet and YouTube. I know this sounds strange but I usually spend an hour a day just learning about something new. You can figure out anything. Like something breaks on my car and I’m like, “I’m not paying someone a few hundred bucks. I’m going to go online for 20 minutes and see how I can figure this stuff out.” I continue to exercise.

I’ve been exercising for most of my life. These things also contribute to my overall goal in business. It was disciplining myself, eating healthy. Besides eating and healthy and exercising, your body is your best investment. Invest in your health. I’d do these things. I’m an avid reader. I love to read. I love to sit down and debate and chat with smart people. I think that’s healthy. I still go to therapy once a week and that’s very helpful. 

BRYAN WISH: Share where you were at 17 years old. 

CHRIS WILSON: At 17, I was in the Washington D.C., Maryland area. Very difficult environment. My mom and myself had been attacked by a police officer and he sexually assaulted my mom in front of me and tried to kill her. My mom survived and because he was a police officer, he lost his job, but he got out of prison and he started stalking our family.

There were no laws against stalking back then in Maryland. I started carrying a gun. All of my siblings were carrying guns. It was around the time there was a lot of gun violence in D.C. and in Maryland. My brother had gotten shot. My cousin had got shot and passed away. My brother survived. I was losing friends every couple of months.

One night, some men came after me and I ended up taking a person’s life and I was 17. I was charged as an adult and while I was in jail, awaiting trial, my brother was attacked again and my dad was killed. Things got worse because I was found guilty and I was sentenced to natural life in prison as a juvenile.

As you can imagine, going to prison is like being teleported to another planet. I fell into a deep depression in my first year in prison because I hadn’t done anything in my life. I didn’t even have a mustache on my face. I was 118 pounds and grown men, who had been in there for 40 years, 30 years, and it was just madness. I kept thinking to myself, “How is my life over?” I had met a person, while I was in there, who had a big stack of computer books and he was teaching himself computer programming and he told me he was going to learn software programming, get out of prison, and start a company and make millions of dollars and buy his dream car.

I remember laughing at him and saying, “Dude, you don’t even have a computer. How are you going to pull this off?” He says, “They’ve taken everything from us but no one can take away the knowledge you put in your head.” I thought about that for a couple of days. When I was in my cell, I took out a piece of paper and I started writing up what I call my master plan. It was kind of like a bucket list. I was like, “I want to get a high school diploma. I want to get a college degree. I want to teach myself Spanish. I want to be able to travel around the world. I want to buy my dream car, a black Corvette convertible with nice rims. I wanted to meet a beautiful woman that was business savvy.”

Most importantly, I wanted to be free again to go back into the community like the ones I grew up in and I wanted to be a positive example. I didn’t know what social entrepreneurship meant back then but I knew I wanted to make money, help people, and provide opportunities. I wrote it up. I sent a copy to my judge and my grandmother because it’s important when you write your master plan, you’ve got to share with people and give them the power to hold you accountable. It’s like a workout partner. I did that and for about 10 years, I just went to school. I got my high school diploma. I went to college. I taught myself Spanish. I went on to study Italian, Mandarin, and even when I graduated from college, I kept taking classes. Vocational, carpentry, sheet metal, and I read hundreds of books. 

Eventually, I had the opportunity after being denied five times, to stand before the judge. I told her the truth. I told her what it felt like to be a mama’s boy and watch your mom be violated in front of you by someone who is supposed to protect us and what it felt like to watch my family members and most of my friends, and two who died in my arms calling for their moms, what that felt like as a young man. There’s no therapy. There’s no, “How do you feel, Chris?” It’s just like, “Get over it. Go back to school. Things are going to be okay,” but they weren’t.

I talked about remorse for the crime that I committed. These men were in their 30s. They came after me. I didn’t want to do it but I had to accept responsibility for it. Then I talked about what I’d do if she gave me a second chance. About how I tested at the top of my class in college while in prison. How I would start companies and create job opportunities and go into the toughest neighborhoods to do this. She gave me a shot and I got out of prison and I went back to school.

It was around the time that my mom found out that I was home and she called me and we talked for about five minutes. She kept telling me, “You sound different, but I just want you to remember some stuff, that I love you, and finish your plan.” She was like, “Remember that I love you.” I said, “Mom, you’re on speakerphone.” Then she hung up. Then my mom committed suicide and she passed away. She actually never got a chance to see me as a free person.

Obviously, that destroyed me but I took that anger and all that pain and I just channeled it into being successful and making my mom proud. When I get out of bed every morning, I like to think that my mom is watching me. I try to be dope. I try to be awesome in every aspect of my life. I’ve been out of prison for eight years now. When I got out, I was homeless. I was unemployed. I was sleeping on my friend’s sofa and waiting on my food stamp card. I was cutting grass. I was just figuring out ways to make money until I got on my feet. 

BRYAN WISH: Thank you for being vulnerable and sharing your story. It’s powerful. When you sat down and made that master plan, when you had a sentence that was pretty much a death sentence, could you see that coming to fruition? Was it hopeful?

CHRIS WILSON: It’s complicated. Like in the book, I call it a positive delusion. I had to believe that I would be free one day. It was the only way that I could study so hard and memorize the quadratic equations in math class because I really believed it. A lot of people around me thought I was crazy. They were like, “Dude, no one gets out. Life means life. That’s it.” I said, “I choose to believe something different.” It was tough.

There were times it’d be six years into my incarceration and my friend will knock on my cell door, “Chris, get up.” I’m like, “What’s up?” “I snuck in a bottle of Rémy Martin. Get your cup.” I’d be like, “I can’t because I’m working on this master plan and I’m going to be out.” My friends would be like, “You’re not going home, Chris.” I had to resist all those temptations. It just worked out. Now it’s a mental thing. Now I’m free. I choose to believe that I’ll be successful. I choose to believe that I’ll try to make the best smart decisions in business or in my relationships as possible. I have to. 

BRYAN WISH: You were up against all odds. 

CHRIS WILSON: Prison is a tough place to be. It’s violent. People lose their lives. All kinds of stuff happens.

BRYAN WISH: You came into prison and within the prison, there are these subgroups that make it even harder to make progress forward. When you had the odds against you, how did you think about the relationships you needed to make and the groups you needed to work within to stay on a positive side of things and not get sucked into an even deeper hole?

CHRIS WILSON: I think I’d have to credit my grandfather who got me into playing chess. I was on a chess team when I was really young, like 10. I’d travel. I didn’t like doing it because my mom would send me away in the summer in chess camp. What it taught me was how to think three, five moves ahead. In an environment like prison, you can kind of see stuff. You see the person who is always gambling or the folks who are up to no good and it’s like, yeah, they might be cool with you but being too cool with them will most likely get you into trouble.

I would also identify with the readers and the guys who were wise. I became friends with these folks. We’d trade books. We’d exchange ideas and we didn’t necessarily hang out together but when I finished a newspaper, The Wallstreet Journal, the old head down the hall that stayed to himself, and maybe he robbed a few banks when he was out on the street, but nobody bothered him, but he had influence. I would say, “Do you want to check the paper out?” I just had good relationships. Folks in the Muslim community, I would walk the yard with the imam and we would just talk about the history and all kinds of stuff.

As a result, because I made relationships with the right people and I was very studious and I mind my business while in prison, they gave me a pass. There were literally times where folks had boiling hot water mixed with baby oil about to splash it on people and they’d say, “Hey Chris, come here really quick.” I’d be like, “What’s up?” I’d get up and they would throw scalding hot water on folks but they were always giving me a pass because I was a good dude and not just because of what I was doing, but I became a mentor at 23 when I was in prison.

Even though I didn’t believe I knew much at the time, I was sharing the things that I was learning. Carpentry skills, entrepreneurship, language studies. I was sharing it with dozens of people in the prison. Some of them were hardcore gang leaders who saw me get my high school diploma in two months and was like, “Can you mentor me?” Then they’d get their high school diploma and figured out they really liked school, pick up a trade, and then get their sentence reduced and go home. I see some of these people in the community. They’ve got families now. They can’t believe they’re out and free and have a family.

That’s really what my book is about, for anyone who just wants to come up with a different plan and live their life differently. It’s not a prison book. We discuss it but it’s about doing something different. It’s about having your own master plan. 

BRYAN WISH: You have been at the lowest lows of life. Family turbulence and life sentence to than the highest highs of life. You’ve gone from 000 to hero in a matter of eight years. It’s incredibly inspiring to have this conversation. What do you think about every day? How do you find your way to fit in or stand out in the world that makes you feel a part of it when your story is so different?

CHRIS WILSON: I think about this a lot. When I was in prison my cell buddy and I had a subscription to The Wallstreet Journal and a couple of other entrepreneur magazines. There were certain entrepreneurs or philanthropists that we’d follow their moves. What we both started to realize is there was not that much difference between them and us.

Obviously, most of these folks were white, connected, and had some privilege. I learned all those later on in business but the thing about the power of knowledge, of just having information, and having the guts to risk it and to do something and to build, that was something that my cell buddy and I started believing in.

Now, when I’m home, I edit some stuff to my master plan. I started telling my friends a year or two ago, I want to have $10 million in the bank after taxes by the time I’m 50. I’ve got 9 years to do it. Some people laugh or don’t take it seriously. Some people sat me down and said, “Let’s talk about how you can get there and what you have to do today to do it.” My point is, I’m not the type of person who will put myself in a box or put a ceiling on myself. I wanted financial independence. That’s what I put on the master plan.

Now, I am financially independent. I don’t think about money. I just work on my creative side. I started painting three years ago. I’ve been selling my art all around the world. I just don’t believe that there are limits to what we all can do if we’re willing to put the work in to do it. If there’s something I think I can do, if there are some books or someone who has been there and done it, I’ll try it. What do I have to lose? I still got stuff I still want to do though. 

BRYAN WISH: It’s admirable you don’t see limits when limits have been placed on you most of your life. Even when there were limits put on you, you saw past the limits. What do the next few years look like for you? 

CHRIS WILSON: A year ago, I started a company called Cuttlefish. Most people aren’t familiar with how clever cuttlefish are as creatures. They can do amazing things. I’ve been selling my art under my company, selling it all over the world. I’ve been writing articles mostly about social justice issues. I’ve been investing some time in a company, APDS, which provides educational tablets to folks incarcerated and they don’t charge the individuals or their family. I have my book on these tablets.

I’ve been going in and just mentoring, just pretty much trying to clone myself and just helping everyone else create their own master plan or making some curriculum that will go on the tablet that will accompany the book so people can create their master plans which I think is super cool. Then I started a Chris Wilson Foundation last year and I’ve been quietly funding art programs, financial literacy, helping returning citizens when they come home.

We also would like to do, at some time, guaranteed lines of credit for social entrepreneurs. That was one of the most difficult challenges for me is not having access to credit. I had contracts but because of my background and probably because of the color of my skin, I couldn’t get a line of credit from any bank even though I had contracts. I want to focus on those things. I’m 41 now. I like to do stuff now like sit in my backyard and work in the garden and plant my flowers and herbs. I still like to exercise. I want to grow old and be wise and enjoy life. 

BRYAN WISH: Thank you for sharing and being you. You have a book. You speak. You have a website. Where can people find you?

CHRIS WILSON: Folks can check my website out, Follow me on Instagram, @ChrisWilsonBaltimore. I’m always painting and traveling all around the world. I’m on Facebook as well, Chris Wilson. I encourage folks to read the book and leave me some reviews somewhere, share it with some folks. It’s a really good book and it’s being turned into a film. I’m working on that now. I hope that comes to fruition.