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How do you survive seven years in solitary confinement? The gift of literacy is what saved Shaka Senghor. Reading, journaling, academic study, and writing books was a way to structure and survive an inhumane, mentally toxic environment. And after 19 years in total behind bars, he was finally able to apply that gift and create employment for himself as a writer and organizational leader upon rejoining society.

Shaka joined Tyler to discuss his book Writing My Wrongs: Life, Death, and Redemption in an American Prison, what it was like to return to society not knowing the difference between the internet and a Word document, entrepreneurialism and humor in prison, the unexpected challenges formerly incarcerated people face upon release, his ideas for helping Detroit, what he connects with in Eastern philosophy, how he’s celebrating the upcoming anniversary of his tenth year of freedom, and more.

TYLER COWEN: Hello, everyone. Today I’m honored to have with us Shaka Senghor, who is the author of a wonderful book called Writing My Wrongs: Life, Death, and Redemption in an American Prison. Shaka spent, I believe, 19 years in prison, 7 years in solitary confinement. We’ll be talking about his experience and his life and all things under the sun. Shaka, welcome.

SHAKA SENGHOR: Thank you so much for having me. I’m really excited to be here.

COWEN: I have so many questions for you because your world is one that’s so far from mine, me being the stereotypical nerdy white guy. But let me start with one. How does one best spend time in solitary confinement? What do you actually do?

SENGHOR: Wow, that’s an interesting question. It depends on who you are.

COWEN: You.

SENGHOR: That’s one of the things, for me — I was really fortunate to be literate. So I took that opportunity to read a lot of books and really do a lot of introspection. Unfortunately, the way solitary confinement is set up in America is really tragic. It’s a very barbaric, inhumane environment, and the level of mental illness in that environment is unimaginable to most people.

For me, books was kind of my escape from that world. Unfortunately for others who didn’t have the skill set to be able to read or literacy, they end up suffering tremendously. There definitely were moments where I wasn’t sure how I was going to survive it or what I was going to do to come out with my sanity intact. The gift of writing and the gift of being able to read was something that really helped me navigate all the emotional turmoil that comes with being in that environment.

COWEN: What kind of books did you read? And which kind of books are more useful or better in a situation of solitary confinement?

SENGHOR: I read everything. I have varied interests. Early in my incarceration, I was fortunate to meet some of the most incredible mentors. These were men who — some of them are dying in prison now. They’ve been in prisons for 40, 50 years. When I first went in, some of them had already had 15 to 20 years in.

They introduced me to books very early on. I remember them trying to be a mentor to me at a time when I was pretty much incorrigible. I just didn’t want to listen. I was really hurting, in a very emotionally tumultuous part of my life. I was very young. I went to prison when I was 19 years old, and I thought my life was over.

I was fortunate to meet these incredible men who saw something redeemable in me. They eventually figured a pathway in, which was through books. The first book that I actually received from them . . . I remember this guy named O’Neil Ill. He wrote books by hand, and he would give me these books to read that he had wrote. They were about Detroit, and what was going on in the street culture. But then he introduced me to an author named Donald Goines, and that opened up my world to the power of reading.

I read everything from fiction to philosophy and sometimes just the dictionary. I’d read Malcolm X’s book, when he talked about him reading a dictionary from A to Z. I was really curious about the etymology of words, so I would study words and figure out where they derived from and how they applied. I also structured my days in solitary as if I was at a university. I would get up and get my workout in, and then I would study a subject each hour.

COWEN: So, a book like Goines, or even Malcolm X — can you get that from a prison library, or is it censored? Or did someone send it to you? How does that work?

SENGHOR: Early, when I first went to prison, you can get all types of books. As I got deeper into my prison sentence, they started banning a lot of those books. Malcolm’s book is probably one of the most popular books in prison because it’s, to me, the one book about personal transformation that just permeates that environment. And it doesn’t matter whether you’re black, white, Native American, whatever. It’s something about his redemptive story that just resonates with people who are incarcerated.

Oftentimes, we exchanged books with each other, and we would buy books. I would order books from different outlets that sold books to men and women in prison. The prison library — it varies from prison to prison. Some are better than others.

Back in the day, you used to get books donated by people. They will have estates, and they would just say, “Hey, let’s donate these to the local prison.” But now it’s becoming more and more restrictive in terms of what you can read, specifically around books that reflect black culture, which was really something that was shocking to me.

A lot of those books I read in the early stages of my incarceration are now banned. You can’t get Donald Goines books the way that you used to. Their excuse is that it talks about crime and things like that. But I’m like, “You can’t get that, but you can get Stephen King, which is murder and mayhem.”

COWEN: Can you get Shakespeare? That’s also murder and mayhem.

SENGHOR: Yeah, murder and mayhem. Yeah, you can definitely get all the Shakespearean classics and things like that. This just reflects the contradictions in larger society.

COWEN: I think you were seven years total in solitary, in one period of four years running. Toward the end of that four-year period, did you feel like you were going crazy? Or did you have some greater, stoic sense of calm?

SENGHOR: When I did the four-and-a-half-year stretch, I went through this moment of really just trying to figure out my life. How did I go from being an honor roll student with dreams of being a doctor to serving all my most promising years in prison? That led me down the path of journaling.

When I did the four-and-a-half-year stretch [in solitary], I went through this moment of really just trying to figure out my life. How did I go from being an honor roll student with dreams of being a doctor to serving all my most promising years in prison? That led me down the path of journaling.

I began to go back and try to unravel the big questions of why and how. Through that process, I began to realize that I had never accomplished anything in my life. So I set out on this journey to write a book and to write that book in 30 days. So I did that, wrote a second book, and started a third one.

Then I fell into a deep bout of depression. I probably had about three years in at that point, maybe two and a half, three years. I was depressed for a few months because I realized this dream that I was discovering — I didn’t have a way to give birth to it. Because I was in an environment where it was just hard to really get my words out into the world.

I was able to navigate that, fortunately. And again, journaling, letters from my father, being able to really talk extensively with him through the written word was really helpful. I would go back and read his letters and read books that inspired me: Long Walk to Freedom, Nelson Mandela; James Allen, As a Man Thinketh. I was constantly just challenging my mind to get through the day.

One of the things that I personally live by and what I discovered is, if you can get through the pain in the moment, you can come out on the other side of anything. For me, it was just about moment-to-moment existence and being fully present in those moments for what they were.

COWEN: There’s a research study I was reading. It suggests that as prisoners come closer to the date of their release, they actually make more escape attempts because the notion of release becomes more real to them. They think about the outside world more. Do you think that’s true? Or do you have a perspective on that?

SENGHOR: I think there’s a lot of anxiety associated with getting out of prison, especially if you’re in a space where you don’t even think you’re ever going to get out. Then that day finally comes, and you look up, and two decades have gone by, and now you’re about to enter a whole new world. What I don’t think a lot of people really consider, when it comes to people who are returning back to society, is that there is this idea of coming into a very foreign world.

The world that I left didn’t exist when I got out. It was a very different world, different people. Most of the people in my life had moved on with their lives while I was incarcerated. So there was definitely some anxiety of how would people look? How would they feel? What would the conversations be like? How receptive would the world be to me returning? And who am I in this new world that I’m returning to?

In prison, I had ascended to being a key decision maker in regards to what happened on the prison yard. Now I’m walking into a new world where I have to create a whole new identity as a free man and as an adult man. I went in as a kid. So there’s a lot of anxiety associated with that.

I’ve seen guys blow their paroles because they get to that door, and then all of a sudden they’re realizing, the mother that was there when I went to prison, she’s no longer here. She’s dead, and they don’t have anybody to go home to. So it’s like, “How am I going to survive in this new world on the other side of this fence?” I can’t say that I’ve seen anybody attempt to escape. But I have seen guys compromise their parole and end up serving more time, as opposed to walking out of the doors free.

COWEN: Do you think solitary confinement can ever be good for prisoners?

SENGHOR: No.

COWEN: In your own story, you seem to give an account where it’s the turning point in your thoughts that occurs during solitary. And that to you is coincidence, and solitary was just terrible?

SENGHOR: One of the things that I always caution some people about, especially when it comes to my story — it’s the idea that solitary made me who I am today. The reality is, the choices I made while I was in solitary is what made me who I am today. It makes me think about our mutual friend. Ben, in the book, is like, “What you do is who you are.”

COWEN: This is Ben Horowitz, yes.

SENGHOR: Yeah, Ben Horowitz. For me, it was more about what I chose to do in that environment, as opposed to the environment itself changing me. Solitary isn’t designed for you to come out better as a person. That’s a very personal choice I had to make in some very tough circumstances. And again, I had the gift of literacy.

I’ve read this book called Cages of Steel, and the book outlined exactly what solitary is designed to do to a human being. Because I was aware of that, whenever I felt those things happening inside of me, I was able to combat that.

If you’re walking into that environment and you’re illiterate or you don’t have access to this information, you don’t know how to deal with being in a cell, being in an environment where people have extremely high levels of mental illness, where it’s extremely hard to find any type of solace because it’s very noisy, very chaotic.

Even with the officers, you see how it transforms them into different people and how they treat the men in that environment. So I can’t say that solitary itself done me any good in that way. I was just fortunate to be able to make choices based on information that I had at my disposal.

On decriminalizing mental illness

COWEN: You also mention mental illness quite a bit in your book, and how common it is in prison. When people receive the sentence, something like “not guilty for reason of insanity” — do you have views on that? Do you think it’s a good idea? We should have more of it, less of it?

SENGHOR: I think that we need to decriminalize mental illness. When I think about solitary confinement, I think about a lot of the guys that I saw end up in that environment. They end up being incapable of getting out because they consistently are in violation of whatever the prison rules are.

But one of the things people don’t think about is that, if you’re dealing with somebody who has schizophrenia, they can’t even comprehend the rules in a way that somebody who doesn’t have it does. Prisons just aren’t equipped to handle mental illness.

In Michigan, when I went to prison — this was 1991, and at that time, my father actually worked in a mental health space, and they just started closing down all these facilities. Those people who would normally get treatment in a mental health facility started ending up in prison. Once they get in, it’s extremely hard for them to get out because the behavior, which is rooted in their mental illness, is in violation of the prison rules. So they continue to get punished over and over and over again.

To me, it’s the saddest and it’s the sickest thing about our prison system that we have because there’s not a lot of transparency. Most citizens who are paying the taxes for these spaces don’t know what happens in our prison. And that’s crazy. When you really think about it, prior to President Obama leaving office, he was the first sitting president in about four decades to actually go inside a prison.

When you think about the reality that we have over 2 million men and women in prison, millions more on parole or probation, and this has a profound impact on our society. We don’t know what’s going on in there. If it wasn’t for people like myself and the many other advocates of prison and criminal justice reform getting out and being able to articulate what has happened in there and what’s happening to people, society would still be ignorant to what’s really going on.

For me, it’s one of the things that inspired me to write the book because I wanted people to know this is what we’re paying for.

COWEN: Before President Reagan, there was a much higher rate of forcibly institutionalizing people into mental homes. Is that part of your ideal solution? Or you think it should just be more treatment and not so much coercion?

SENGHOR: I think that in a society that has as many resources as we have, it is ridiculous to think that we can’t treat people outside of facilities. I think people do better when they are in spaces where there’s holistic healthcare, holistic mental-wellness care. To think that we can’t do that, given how much money we spend on prisons, is pretty much a bit ridiculous. And it’s rooted in what prisons really are.

They’re an extension of shadow slavery, which you know is a reality of our country. You think about the 13th Amendment, which was supposed to eliminate slavery — it actually created a loophole for slavery to reemerge in a new way. And as you know, you see that in prisons, where you get this cheap labor and oftentimes free labor, and people are exploited and have been exploited for years.

But now, I think both parties are realizing it’s coming at an astronomical cost to the rest of society. This is where you’ve seen a shift in terms of criminal justice reform.

COWEN: You mentioned in your book, I think, that there were 36 cases of misconduct brought against you. Were you guilty of those, or are they trumped-up charges? Or how do you think about them?

SENGHOR: No, I was pretty much guilty of all of them.

COWEN: They never trumped a few up? That’s amazing to me.

SENGHOR: [laughs] I’ve been in trouble for some things that I didn’t do and definitely had, but those actual misconducts, I think I pretty much did all those. When I went to prison, what I didn’t realize is that I was still suffering from PTSD from when I got shot at the age of 17. And going to prison, a very volatile environment, compounded that PTSD.

When I went to prison, I thought my life was over. I didn’t think I was ever getting out. I was 19 years old, looking at 17 to 40 years, with 40 being the only guaranteed time. And as a 19-year-old, you can barely see two weeks down the line, let alone two decades. So I acted out of that emotional instability that most young guys act out of when they’re in an environment that’s very volatile — a lot of fights, a lot of rebellion.

For me, it took years to really just . . . the maturing nature. Even now, out here in California, they recognize the brain science that the brains of kids don’t actually mature until they’re about 25, 26. So you’re still considered a juvenile at that point. Imagine if you’re 19 years old, you’re thrown into this volatile environment, and you’re told that you have to be a model prisoner in order to get out. It’s not realistic that that’s going to happen.

And the other part of it is that it’s a very antagonistic environment. It took me years to develop empathy and compassion for the officers that actually work in the environment, and it actually occurred to me when I was leaving off a visit. Anytime you go on a visit in prison, when you come out of the visit, you have to get strip-searched. I would always wonder, “Why is this officer so antagonistic doing the strip search?”

And then I would just realize, his job is to look at buttholes 40 hours a week. That can’t be a pleasant job to have. To think that this is your job, this is your life. This is how you earn your livelihood to take care of and provide for your family. The reality is that you’re going to be impacted by that.

And you’re talking about every matter of buttholes you can think of: shaven, unshaven, fat, slim, clean, unclean. And this is a job that people have. You have to imagine that it’s not comfortable being in that position. What does that do to a human being? How does that change you, when you’re seeing people at their worst and most vulnerable moment as an occupation?

Then you have to figure out, how do you treat these people with dignity when your job doesn’t even have dignity in its title description? So for that, you start to think about how people are impacted and why the environment becomes so antagonistic. And it starts to all make sense. So, yeah, I got into a lot of trouble.

COWEN: Outside of the prison, do you think the prison guards are as nice as everyone else? Or do you think they’re systematically different? How nice are they as a class of people?

SENGHOR: The reality is that in most of these environments, you’re talking about very rural prisons. You’re talking about low education and easy entry points to an environment. You’re talking about racial dynamics.

I grew up in a city that’s predominantly black, in Detroit, but every prison I was in was predominantly run by white guards from rural communities. So there’s an instant antagonism because in a lot of instances, their first interaction with people of color is happening in a very volatile, very antagonistic environment. And you know, it’s hard to come out of that environment and be a nice person.

I was really fortunate to meet people in that environment that were just good people. I’ve worked for a guy, my recreation supervisor, named Tom Scheidt. He’s one of my good friends to this day, and he’s one of the men who I worked for in that environment that was super compassionate, super thoughtful. We worked in a tough environment, the recreation center. When we come out for yard, you’re talking about 300 guys that’s locked in this one building. It’s one officer and one rec supervisor and maybe sometimes two recreation supervisors.

The thing that made Tom special is he always acknowledged our humanity. He always was thoughtful about how he engaged us. He always was trying to inspire the best in us. So I’m always conscious to not portray everybody who works in the system as bad people because there are people who are well meaning and good intentioned. It’s just a tough environment to maintain that when you’ve been in it for so long.

Even in California, I’ve worked with people in the CDCR [California Department of Corrections] who are just incredibly thoughtful about, how do we transform the spaces to where you can help men and women come home healthy and whole? Unfortunately, it’s just not the norm around the country.

COWEN: So there’s a rebellious side in your past.

SENGHOR: Absolutely.

COWEN: And there’s a productive side in your present: writing this book, all the other things you’re doing. How do those two things fit together? Does the rebellious side of you, channeled, now give you greater productivity? Or how do you view that?

SENGHOR: I think of it all as energy and how you choose to direct the energy. When I was inside, in the early stage in my incarceration, I mismanaged that energy in a way that happens when you’re emotionally undeveloped. But as I began to develop and mature as a man, I began to channel those things into productive outputs.

And it’s all about identity. I went in with a distorted identity of who I was as a person. I grew up in an environment that tells you that your only outcomes can be an early death or a prison sentence. So that behavior and that narrative is normalized. It wasn’t until I began to change the narrative internally by finding ways to add value to my life, by finding ways to self-identify in a way that was healthy and whole.

Now, there’s definitely that rebellion, When I got out of prison, I was so optimistic. I just thought that people would say, “Okay, he served his time. He wants an opportunity to be employed. He just wants to create a space to be a productive citizen.” And sadly, the way society is set up, that’s just not our norm. It’s hard to find employment.

So, I’ve had to always create employment opportunities. Again, I’ll reiterate this over and over: literacy played a major role to me becoming who I am today, and having a skill set as a writer — it created my first employment opportunity.

For me, that energy is still rebellious, but it’s rebellious against injustice. I use that energy, and whenever I find myself angry at an injustice, it’s what can I contribute as a human being to change that? To help other people think about things differently, to bring people in proximity to spaces that they normally wouldn’t be in. Again, it’s just directing the energy in a productive way.

On entrepreneurialism in prison

COWEN: And prisoners as a whole, at least if circumstances had been different, do you think they’re an especially entrepreneurial group?

SENGHOR: I’ll start with reframing that a little bit. One, I am vehemently opposed to calling people who are incarcerated “prisoners.” One of the reasons that I am that way is because these are men, these are fathers, they’re brothers, they’re sisters, they’re sons, they’re daughters, they’re mothers. I think that until we can identify and recognize their part, it’s hard for us to help them.

COWEN: What should we call them?

SENGHOR: Humans.

COWEN: Okay, but we need “humans who are in prison.”

SENGHOR: Yeah, absolutely.

COWEN: Yeah.

SENGHOR: Men and women who are incarcerated. A lot of us come from a culture where hustling was part of our survival. And what I found in my own ability to be successful in a world where they’re constantly telling you that you can’t get employment or you can’t get housing is that the skill sets I learned in the streets from hustling are transferable.

So when I got out of prison, I hustled books out of the trunk of my car. I didn’t start off with being a New York Times best seller with a published book by a major publishing outlet, Convergent and Penguin Random House. I started off self-published out of the trunk of the car. And basically, I used the same model that I used when I sold crack cocaine. It’s like you buy low, sell high, and you create profit or create margins based on how you invest.

Even with networking — I learned that in the street. I learned that in order to survive in the street, you need to have allies in different areas. And you need to have partnerships if you want to be successful as a drug entrepreneur, a pharmaceutical, [laughs] a street distributor. You need to figure out how to be networked in not even just different neighborhoods but in different cities. So those are transferable skills.

The leadership that I developed in the street culture and in prison . . . even in an underground market in prison, I ran a lot of the hustles in there early on. Basically, I would run what we called sucker stores or black market stores, and they have an incredible margin. You buy one product from me; then you owe me two when you get your money.

That skill set transfers to any entrepreneur endeavor, and a lot of men and women in that environment have that skill set, but they also have many other skill sets. There’s brilliant artists in that environment. There’s brilliant singers and athletes and creators. And I think it’s one of the spaces where, now, people are starting to realize we’ve been throwing away talent. And always think of it from this perspective, right?

I was a fellow at MIT Media Lab, and I did a prison hack there one day. Basically, I gave them five design challenges based on how we survived in prison. And they were as complex as making a tattoo gun out of a tape player motor or ink pen and a guitar string, on to making a lighter out of batteries and wire. These are things that men inside prison do all the time to survive. When I did this hackathon, none of the students were able to complete it in the time that was allotted. It was about three hours.

You go in any prison, and guys will complete that task in 30 seconds. When people get caught in there, they’re put in solitary. You make a tattoo gun, you’re put in solitary. Whereas if we’re really thoughtful about what are the best outcomes we can produce, how about we get this person in the engineering class and figure out how they can utilize that skill set when they get out of prison, as opposed to punishing them for figuring out how to survive?

COWEN: What’s the most common medium of exchange in prison? You mentioned doing these deals. What’s the central item traded? Is it dollars? Is it cigarettes?

SENGHOR: When I first went in, it was cigarettes. Cigarettes was pretty much the most steady currency. Then that was taken out because they banned cigarette smoking in prisons. Then stamps became the currency because you could send stamps to the free world and have your family exchange that for currency. And then it becomes food and cosmetics. So soap has value in prison — you can trade that off for food and things like that.

Everything has currency, and it’s one of the things that’s interesting about the environment. When you think about the history of currency in the world, where back in the day, you just bartered and you exchanged things, and the same thing happens in prison. What I learned from that is that money is only based on the idea behind it and what value you assign to the idea behind the particular form of currency you choose to exchange. And the same thing is in prison.

COWEN: The individuals who are incarcerated — what are their senses of humor like? Is it different on the inside or just the same? Are they funnier?

SENGHOR: It is probably one of the most fascinating, quick-witted spaces you can imagine. I did an interview some years back with Trevor Noah, and I remember telling him like, “Prison is hilarious.” And he was like, “No, no, no. That doesn’t seem like quite a good narrative.” [laughs] But what I would always explain to people is that you can’t survive that environment without the ability to laugh at the absurdity of it, the ability to laugh at the craziness of it, the creativity of it.

And you have some brilliant, brilliant comedians in that environment. There’s actually a comedian who’s free now, Ali Siddiq, who’s just an incredible storyteller, and he’s a great comedian. And that talent is abundant in that environment. Guys crack jokes all the time. The officers crack jokes. It’s one of the things that is universal — laughter — and you need that in order to survive hardship.

On the biggest change in the world after getting out

COWEN: So you’re removed from a big part of the world for about 19 years, and then you get out. Put aside the law, crime, prison — all those topics. Just think of it as having been somewhere else for 19 years. What to you is the biggest surprise when you’re out again? Not about how people perceive you or anything to do with that, just the world.

SENGHOR: Technology was unbelievably shocking.

COWEN: What in particular?

SENGHOR: Everything. When I came home, I remember the first time —

COWEN: The year you went away, again, is —

SENGHOR: I went in 1991.

COWEN: Okay.

SENGHOR: This is before the internet was even a thing, right?

COWEN: Right.

SENGHOR: So when I came home and I realized you can Skype people — that made me think about The Jetsons, the things that I grew up as a kid watching and we never thought would be possible. Cars that talk, telephone and smart technology. All those things were overwhelming. They were fascinating, but also a bit overwhelming because I realized that in that 20 years that I had been gone, the world had created a whole new language.

So when I came home and I realized you can Skype people — that made me think about The Jetsons, the things that I grew up as a kid watching and we never thought would be possible. Cars that talk, telephone and smart technology. All those things were overwhelming. They were fascinating, but also a bit overwhelming because I realized that in that 20 years that I had been gone, the world had created a whole new language.

Even in the 10 years since I’ve been home, so much has changed in that time period. So it was just a quick, fast learning curve.

When I got out, I remember the anxiety. I didn’t even know the difference between a Word document and the internet. I remember every time I was getting ready to save a Word document, I would always ask, “Is this going to get a computer virus?” Because I didn’t know the difference between those two things. So I had a quick learning curve. I had to learn all this new language. And I’m a nerd too, so I’m just a cool nerd.

[laughter]

But I love it. I love learning. I love the idea of how to utilize this as a writer and as a content creator. It was just fascinating to come out and discover this fascinating technology and all the different ways it allows us to connect today.

COWEN: What about social mores? Did anything surprise you?

SENGHOR: I would say, socially, the thing that I’m most shocked about and shocked by now, especially given the prominence of social media in the world, is how mean-spirited people are toward each other and toward people who just have different beliefs. And how easy it is for us to just cancel people because they don’t believe what we believe, or they don’t see things the way that we see things.

It’s like the world that we live in now seems to be very volatile in terms of human interaction. I think what social media has done has really just exposed us for who we truly are.

In years past it was easy to kind of mask racism, and mask gender bias, and mask misogyny and all these different things because we didn’t have this level of transparency that we have now. I think that this is part of our growth. You have to have that transparency. You have to have something that challenges the way that we think, the way that we see things. And when you have that, it’s very uncomfortable early on.

But hopefully — and maybe this is just the optimist in me — I think we’ll get through these rough periods and find what I believe is our common core values of being humane and compassionate toward each other.

COWEN: So you think racism is perhaps, today, more transparent, not necessarily higher, but more in-your-face and more disturbing?

SENGHOR: Yeah, absolutely. I’m not even disturbed by it because I know that this always exists. I know that’s one of the things that, when you are in an environment like prison, it’s super present. And it’s very clear that we live in a very racist society.

It’s when you get out to society and you realize racism shows up in different ways, though. There’s systemic racism, there is implicit bias, there’s ignorance, there’s blatant overt racism. And I think the reason that it exists in the form that it exists in is because as a country, we’ve been cowardly in just saying, “Hey, this is what has happened here.”

We’re coming up on 400 years. The New York Times is doing this incredible study or examination of the 400 years since 1619, when the first enslaved people were brought to the shores of America. When you think about that, it’s been 400 years that we haven’t had an honest conversation. We haven’t had a national apology. And I think until we have those things, we’ll always grapple with the reality of racism in America and how it permeates so many aspects of our culture.

To me, I think it’s just cowardly and lazy thinking because once you can say, “Hey, this was really a terrible thing that’s happened and to happen to other people, and we see how it impacts other people, and we see how systemically it hurts and harms people,” then you can have a real conversation.

COWEN: Other than your own book, what book or movie do you think best captures life in a US prison?

SENGHOR: What book or movie? Hmm, that’s a really tough one. I think it’s really complex. I don’t think we’ve had any real good movies in a long time about the American judicial system, in general. I think there was a show, The Night Of, on HBO that was really interesting, and I think it highlighted some things. Surprisingly, I would say Orange Is the New Black was really more accurate than people would believe.

I think When They See Us, specifically the fourth part of that, was really intriguing in terms of showing people how the system is so flawed. From a documentary standpoint, what Ava DuVernay did with 13th was just brilliant because it connected all the dots between the 13th Amendment and what’s currently happening in terms of mass incarceration.

There was the Kalief Browder movie, which was really about this young man who was accused of a crime he didn’t commit, and he went through two years of solitary confinement. When he got out, he was unable to unpack all the things that happened to him and eventually committed suicide. I think that was just such a tragic story and a narrative that we should all keep our eyes on because it’s happening to so many people.

But I definitely think we’re poised for something that’s more about the human journey, and what happens to humans on the inside, and what even leads to people being in prison. I’m hoping to be able to add to that narrative in some way soon.

COWEN: A much older book, Jack Henry Abbott, In the Belly of the Beast. Do you know it?

SENGHOR: Yeah, I haven’t read that one. I’ve read a lot of books about prison, probably more than I care to remember. I think the redemptive stories are super important and needed.

On religion in prison

COWEN: Would you say that in prison you, in some way, discovered religion?

SENGHOR: I grew up in a household where my mother went to church, in a community where church was a big part of that experience. So I wouldn’t necessarily say that I discovered religion in prison. I went through several iterations of figuring out what my spiritual journey is. I’ve studied Christianity. I’ve studied Islam. I’ve studied Buddhism. And what I realized for me personally, that my spiritual journey is really about learning, an ability to connect with other human beings.

To me, I think the greatest scripture ever written is nature itself. If you think about the infinite nature of the sky or the depth of the ocean — to me, I think that’s metaphors for who we are as human beings, like our infinite ability to connect and the depth of which we can really stretch our imagination across any sector if we’re present to it.

Meditation is a big part of how I live my life. Mindfulness — being super present in the moment — is really important to me because I think the moments are all that we have. I studied religion a lot early on in my incarceration, largely influences of Malcolm X and his journey — that self-discipline that he was able to develop through his religious practices. And just the curiosity, like historically, what we’ve thought about a divine power bringing all of this magic into the world as we know it now.

I’m still on that quest, still on that journey. I’m still learning. That’s the thing I love about life — every interaction is an opportunity to learn.

COWEN: Do you think of yourself as a black Muslim the way Malcolm X was?

SENGHOR: No, I no longer subscribe to the Islamic faith. I actually haven’t subscribed to that faith in years, in decades. Some of the principles of all the faiths — it’s one of the things that I love, is that I can pull from any of those tenets and doctrines something that’s useful and meaningful to my life spiritually today.

I probably study more Eastern philosophy than anything because I’m really about self-governance. I’m all about personal responsibility and accountability, and I don’t think that you have to deify that in order to be successful and to be spiritually connected. I think that it’s just a pathway to deeper learning when you don’t have the restrictions of somebody else’s dogma.

COWEN: The Melanic Islamic Palace of the Rising Sun — what role do they play in prisons?

SENGHOR: It was a very small group within Michigan prison. Very unique, and it formed in Michigan’s prison. It was really a combination of social activism with a religious theory behind it. The group has legally been disbanded in Michigan prisons because it was labeled as a security-threat group.

But it’s one of the spaces where I learned the most about life and how I wanted to show up in the world. It was through that pathway that I got introduced to a wealth of knowledge, and the ability to study and learn and be disciplined in my practices. It played an integral role in my development as a man.

COWEN: And you became a manager of sorts, a kind of personnel manager.

SENGHOR: Yeah, I was a leader. Every space there, every prison has its own temple or its own space of practice. I was oftentimes either the education director or the spiritual adviser. And as a spiritual adviser — it comes with a great deal of responsibility. That’s the equivalent of being a pastor or deacon or whatever name is for the church or an imam for the Muslim faith.

With that pathway of leadership, I really was able to grow in terms of understanding how you practice what you preach. Because it’s very difficult to do in prison. It’s a very volatile environment. But it was through that pathway that I was able to refine my own personal principles and evolve as a leader.

COWEN: If you’re looking for a deputy of sorts to carry out some task reliably or to be allied with you, what qualities do you look for? How do you spot talent? You as venture capitalist, so to speak?

SENGHOR: As a VC, if I was a VC.

COWEN: You have been a VC.

SENGHOR: Yeah, basically, of sorts, right? To me, it’s people who can honor and actually follow through on what their word is. Innovative thinkers, people who are thinking about not only their personal agenda, but how does what they bring to the table add value to the organization? I’ve been executive director, CEO of organizations since I’ve been out of prison. And in my hiring practice, it was always about what are we missing in the company that we really need?

Listening to Ben [Horowitz] sometimes, who’s not only a great friend of mine, but he’s like my default mentor. I don’t know if I’ve ever even told him that, but he’s such a wealth of wisdom. And one of the stories he tells is about talking to a woman who runs an all-women-based company. He asked her a question about why, and what does she look for, and she said helpfulness, and that women oftentimes are more helpful than men.

What I think of in hiring practices or in recruitment or partnerships or things like that is, what are the skill sets that I’m lacking? Because otherwise you end up hiring somebody who’s like you, and then you’re just running down the same railroad, and you’re not able to accomplish as much. So I’m always thinking about what are the skill sets that I don’t have or what my organization — Now, I’m building out my own creative content company. And I’m always thinking, “Okay, what are the skill sets that I don’t have?” I know I can create the content. I can deliver the content. But what are the intangibles that I need in order to be successful as a content creator in the world? It’s always those things that often fly off people’s radar.

In prison, there were different things that were needed. When you’re running an organization in that environment, your preoccupation is with safety. But it’s also with how do you create allies, and that’s a different skill set. So you’re looking for somebody who’s diplomatic, somebody who understands how to create space for both parties to walk away with their manhood intact and with their safety and well-being secured. So it’s always about those intangible skill sets.

COWEN: It seems to me, from my great distance, that a lot of men in prison have women on the outside who are very strongly attracted to them. How do you think about that? Why do you think there’s a special attraction to men in prison?

SENGHOR: [laughs] I mean —

COWEN: Or do you think it’s not true?

SENGHOR: No, I think it is true. I think part of that narrative —

COWEN: And beautiful women, too, especially beautiful women.

SENGHOR: Yeah, I think there’s a few things that happens. One is, there is the intrigue of mystery, like who are these men? There’s also the power dynamic. Somebody who can survive that environment — there’s something powerful about that aura that attracts people into that space. I think there’s also the refining of the principles that oftentimes are sought out: the intelligence, the cultivation of emotional presence.

And then there’s also the other part of just the safety of knowing that this person isn’t out here running amok and that they have their undivided attention. So those relationships can be healthy and productive, or they can be very unbalanced and dysfunctional in a different way. But it’s all types of relationships that show up in that environment.

On Detroit

COWEN: Now, you’re from Detroit. Let’s say a philanthropist came up to you and gave you the power to give away, say, $20 million to Detroit in some way. Do you have any thoughts on how that money should be spent?

SENGHOR: Absolutely. I love my hometown. I live in LA now, and I love LA. But I have a personal, deep relationship with Detroit, and I think Detroit is one of the greatest places for hustlers and grit. You can’t survive in that city without being a hustler or having some type of grit.

Detroit is essential to the fabric of America in a way that people don’t often think of. The automotive industry — that’s where it emerged, in Detroit. So without Detroit, there’s no car industry. Motown music — I don’t know many people who have not heard a song from Motown in various ways. We’ve contributed mightily to American culture.

But what I would create would be a very high-level tech-inspired entrepreneurial school, a school for hustlers that includes all the technology, but also even in vocational. I think that those trades are often overlooked, and we live in an economy now where people are looking for laborers in carpentry and electricians and plumbers and things like that. So it’d be a hybrid school of technology and vocational. But with that Detroit swagger added to it.

COWEN: What from the history of Detroit music is especially important to you?

SENGHOR: The history of Detroit music — man, there’s so much. When I think about Motown, I think about the brilliance of Berry Gordy to really find and discover talent that was just blocks away.

COWEN: One of the best venture capitalists of the century, right?

SENGHOR: Absolutely, absolutely, I think one of the greatest entrepreneurs, the greatest curator of talent. And when you think about where the talent came from — Diana Ross was in Brewster projects, and so much talent was right in this little two- or three-mile radius — that part resonates with me.

But the other thing that really excites me is techno music, and a lot of people don’t know the roots of techno music being in Detroit. Now, we have all this music — I think they call it emo, EDM. They have some fancy name for it now, but it’s rooted in techno music. And the architects of that music grew up in Detroit and started there.

When I think about music culture, those things really matter to me. And of course, Marvin Gaye and What’s Going On. It’s so timeless, and it still applies to where we at in America right now. The musical legacy there is just unparalleled.

COWEN: Do you think that hip hop music today is a revolutionary or a conservative force?

SENGHOR: I think it’s revolutionary. It’s the most influential culture in the world right now. There’s nothing more influential in terms of music than hip hop. Hip hop as a culture, but rap specifically as an element of that culture. And I’m fortunate to now be in conversations with a lot of artists. I just spent some time with T.I. on a panel in Atlanta where we got a chance to talk about criminal justice.

Basically, you have these artists who are using their platform to talk about social impact. I just spent time with Nas, who inspired me when I was incarcerated, like his song “One Love.” I felt like it was a personal letter to me. So to be able to come full circle through our relationship with Ben and spend time with him and just show him how his music is inspiring people to think about life differently.

There’s nothing more revolutionary than turning around the hearts and minds of men who are in environments where there seems to be no hope. I still think it’s revolutionary, even though a lot of it’s been commercialized. I’m always finding artists who are really pushing the envelope — artists like J. Cole and Kendrick Lamar who are doing super innovative things and shifting the way that we see the world.

There’s nothing more revolutionary than turning around the hearts and minds of men who are in environments where there seems to be no hope. I still think it’s revolutionary, even though a lot of [hip hop has] been commercialized. I’m always finding artists who are really pushing the envelope… doing super innovative things and shifting the way that we see the world.

COWEN: Which do you prefer more, Middle Eastern food or muffins?

SENGHOR: Middle Eastern food by far. Detroit —

COWEN: Excellent in and near Detroit, right?

SENGHOR: [laughs] Absolutely. Some of the best food outside the Middle East definitely happens in Detroit. I love that food, along with soul food, which is my next favorite.

COWEN: If you think about your life and where your life will go, do you see traveling to many different places as an integral part of what you will learn next? How does travel fit into your vision of yourself?

SENGHOR: Absolutely. I’ve been fortunate to be able to travel a lot. I’m coming up on 10 years of freedom.

COWEN: Where do you want to go? And how do you think about where you will go?

SENGHOR: I’m actually kicking off my ten years of freedom this weekend.

COWEN: Congratulations.

SENGHOR: I’m celebrating with Ben. Ben is treating me to an amazing weekend of just sports engagements. It’ll be like a brother weekend. It’s kind of funny because people will be like, “Y’all got a bromance.”

But he’s just an incredibly thoughtful friend, and his wife Felicia, who’s like my big sister — they’ve been so kind and gracious in helping me really celebrate life. They’ve given me an abundance of gifts in the way of life experiences and saying, “Hey, you should go out and just celebrate. You’re free now.” So we’re going to kick that off.

Then December, I’m taking a trip to Ghana for two weeks —

COWEN: Great country.

SENGHOR: It’ll be the first time that I’m actually taking a real two-week vacation. I’ve had other cool trips. Felicia and I went to the Dominican Republic a few months back, earlier this year, and that was an incredible experience to go over there and just explore that country.

So I’m celebrating by doing 10 crazy different experiences. Some of them require travel. I’m going to Tokyo at some point. I’m going to skydive, probably around the celebration anniversary of my freedom. It’s really about taking a leap of faith because under any other circumstance, I never would have been just jumping out of an airplane.

COWEN: I’m afraid to do that.

SENGHOR: I don’t even know if I’m afraid yet. I just didn’t think it was something I would be doing, but I’m going to do it. I think fear is all the reason and motivation to do it. The more fears you conquer, the more pleasant life becomes.

On the problem of recidivism

COWEN: If you’re thinking about the problem of recidivism — people who upon their release commit crimes again — what do you think we can do to improve our accuracy of who will commit crime again and who will not? Do you feel we’re optimizing now, or it’s all screwed up?

SENGHOR: I think a couple of things about recidivism that people don’t know is, one, most people who go back don’t necessarily go back because they committed a new crime. Oftentimes they go back because they’ve committed a technical parole or probation violation.

There’s an organization that’s led by Van Jones called Reform Alliance, who’s doing some incredible work about reforming the probation system. That’s based on the rapper Meek Mill. He was incarcerated. He was sentenced to two to four years for the most ridiculous probation violation. He popped a wheelie in New York and broke up a fistfight with his friend and some guy who accosted his friend, and they violated his probation and then sentenced him to two to four years.

A group of us — when I was working with #cut50 that was led by Jessica Jackson at the time — we created a campaign, the Free Meek Mill’s campaign along with Roc Nation. Now they’ve shifted that into a whole new movement to end probation, technical probation and parole violations.

So one of the things is the restrictions that people have. Say, for example, I was out on parole, and I was jaywalking, and an officer approached me and said, “You know what, you’re jaywalking. I’m writing you a ticket.” I have to go report that to my parole officer, and my parole officer can decide whether to violate my parole because I’ve come in contact with law enforcement again.

People go back for stuff as ridiculous as jaywalking. People go back because they can’t pay fees and fines, and if you can’t pay your fees and fines, you end up getting your parole violated. It’s kind of ridiculous when you think about it because it’s so hard to find employment. To disrupt that, one, we need to do away with these technical violations.

Secondly, we have to create space for people to find employment and housing. When I got out of prison, I didn’t know that it was legal to discriminate against people with a felony in housing. I didn’t know that it was legal to discriminate against people with a felony when it comes to, in some states, voting.

So you can pay taxes, but you can’t vote in some states. You can be barred from employment by having a felony on your record. A lot of people don’t even know that you can actually be charged more for life insurance if you have a felony. You can’t use TSA, which our taxes pay for, if you have a felony.

There’s literally 40,000 collateral consequences of having a felony on your record, so it’s exceptionally hard for people to get out of prison and to not only survive but to thrive at any level. So people oftentimes end up resorting back to hustling just to take care of themselves and provide for their family. I think those things are easily fixable.

There’s literally 40,000 collateral consequences of having a felony on your record, so it’s exceptionally hard for people to get out of prison and to not only survive but to thrive at any level. So people oftentimes end up resorting back to hustling just to take care of themselves and provide for their family.

COWEN: In prison, did you have to pay those crazy fees and fines we read about, like 10 times the normal price for a phone call?

SENGHOR: Yes, absolutely. At one point, it was costing about $15 for a 15-minute phone call, literally a dollar a minute. They’re not as high now, but they’re still higher than what we pay. Even now, to talk to my friends, I have to pay five or ten cents to send them an email. But I can send emails to anybody in free society all day for free. And I still pay for their phone calls when they call. It’s probably about $3 per call now, far more than what I pay for my phone bill.

It’s just ridiculous how that environment exploits the families of men and women who are incarcerated, and oftentimes these families are poor and can’t really afford to stay in contact with their family members or go visit them.

COWEN: Some people argue that if we either legalized or decriminalized drugs, this would make for a better nation and also improve our prison problems. Do you have an opinion?

SENGHOR: Absolutely. I think that the choice to use drugs are personal choices and that adults should be able to choose what they do with their bodies. When I personally think about inner city life and conflicts that happened, most of the conflicts happened as a result of using alcohol as opposed to using drugs.

I don’t know many weed smokers that want to do anything other than eat good food and watch comedy and laugh or do something creative. Whereas alcohol, on the other hand, oftentimes can be very volatile. So I just think we overlegislate people’s lives in a way that’s not healthy, and we see that now with places where marijuana has been legalized. You haven’t seen an increase in crime. If anything, you’ve seen a decrease.

The unfortunate part of that is that the people who in the past have been sentenced for drug-related offenses are finding it really hard to enter that industry and make money off that. The same people who, at one time, was creating laws to incarcerate people are now creating laws that are creating opportunities for their friends to financially benefit. I think we need to change that model and make it easier for people who were at one time incarcerated to engage in that industry.

COWEN: Should we all just stop drinking alcohol, voluntarily, but stop altogether?

SENGHOR: No, because I love tequila, so I’m definitely not signing up for that. But my point in raising that argument is, again, it’s up to individuals to do these things responsibly, and if not, then you accept the consequence that comes with irresponsibility. I don’t think that that should be any different with the usage of marijuana.

I can’t say about other drugs. I still think it’s a personal choice that people make. I’m not going to advocate for people to become opioid addicts, but I think decriminalizing it can definitely figure out different ways to deal with that. I think people who have opioid addictions or any other Schedule 1 drug addiction should be treated as opposed to incarcerated.

COWEN: Some employers now — they’ve stopped asking job applicants if they have any kind of criminal record. Do you think this has a major positive impact, small impact, no impact? Any opinion?

SENGHOR: I think it has a major positive impact. For example, in June, I stepped down as the executive director of an organization here in LA called Anti-Recidivism Coalition. It was founded by Scott Budnick, who’s most often known for producing the movie Hangover. But he founded this organization about six or seven years ago now, and the idea was to help men and women return to society healthy and whole.

One of the things that we did at that organization is, we hired most of the staff. So when I left, about 68 percent of the staff was system impacted, meaning that they had been in prison from anywhere for 3 years to 30 years. I can tell you, some of the best workers with the highest skill set, highest level of commitment that you can ever imagine. Us being on time means being an hour early.

We also created partnerships here in LA with vocational trades. A lot of our members are actually building the current LA stadium, the new Rams stadium. There’s a lot of our members who are working in the film industry now as a result of this organization.

The firefighters — we know that the wildfires are a major issue, especially now, here in LA. We created a partnership with LA Fire. We created a fire camp in Ventura where formerly incarcerated men are now getting employment to fight these fires, and they’re very committed. The way that we show up in these spaces, people rave about their work.

For me, it’s really about do we create opportunities that give people hope that they can contribute to society in a meaningful way? I promise you that when you hire people who are system impacted, you’re going to get some of the best employees ever, and they’re going to show up in a way that’s going to make other employees have to step their game up.

The more that we’re doing that, the more that we’re normalizing that these are people who had a moment in their life where they were at their lowest point, and that now we can create an opportunity for them to engage in a way that contributes a great deal to society — I think it’s groundbreaking, and it’ll change the world.

ARC, Anti-Recidivism Coalition, is currently being led by a guy named Sam Lewis who spent 24 years in prison. And now he’s running the organization that has a big staff, two offices — one in LA, one in Sacramento — and they’re just doing incredible work over there.

COWEN: My last two questions — they’re both philosophical. First, at several points in your book you talk about the ethical code of not ratting on other people.

SENGHOR: Yeah.

COWEN: Do you view that in pragmatic terms, something you think is just the right way to be? Is it a view you’ve moved away from? Did having other people rat on you change your view at all? Where do you stand on that ethical code right now, today?

SENGHOR: I get asked that that question often. I grew up in an old street code, where if you are agreeing to participate in this culture, you’re agreeing to all the consequences that come with it. That means that if you and I commit a crime together and I get caught, then I have, within that code, to keep my mouth shut. Me telling on you or giving you up — that violates that code, and that’s just a principle thing.

As a man, I still stand by that principle. I’m not going to do anything that I can’t handle the consequences of, and I’m not going to give somebody up to lessen the burden of those consequences when I agreed to this culture.

I think what people often miss when it comes to the no-snitching code is, they try to apply that to citizens, and it doesn’t apply there. If somebody breaks in your car and you are a working citizen and you report that to the police, that’s not snitching. That’s making sure that you get your insurance paid as a citizen who pays taxes and that you’re provided with the services of the officers.

Fortunately for me, I don’t live in the street code anymore, and I don’t live in that culture. So there’ll never be a circumstance where I have to put that theory to test again in my personal life. I prefer people don’t engage in that culture at all, but I always tell the young guys that I mentor, if you’re going to make that decision to participate in this culture, then you have to be prepared to deal with all the consequences that come with that.

COWEN: Final question — is it worse to do injustice or to have injustice done to you?

SENGHOR: I think it’s worse to do injustice. It’s unfortunate when you’re a victim of an injustice, but to consciously be unjust toward other human beings — I think that’s far worse than what they end up experiencing as a result of your injustice. So, if you have a choice to be just, I always would choose that over being unjust.

COWEN: Shaka Senghor, thank you very much. And again, for our listeners, I very much recommend Shaka’s book, Writing My Wrongs: Life, Death, and Redemption in an American Prison. Thank you.

SENGHOR: Thank you so much for having me.