Pod Insights a16z Podcast How to Be Free: Shaka Senghor, Oprah Winfrey, Ben Horowitz About this episode Taken from The Oprah Podcast, this special episode brings together Shaka Senghor, a16z cofounder Ben Horowitz, and Oprah Winfrey for a powerful conversation on resilience and transformation.
Shaka, a resilience expert, motivational speaker, and bestselling author of Writing My Wrongs, shares his journey from incarceration to redemption along with insights from his new book, How to Be Free. Full of hard-earned wisdom and practical tools, it’s a guide for anyone seeking freedom in their own life.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:02 Speaker 00 Today, we're sharing a conversation from the Oprah Podcast with author Shaka Sankor about his new book, How to Be Free. He and Oprah talk about escaping life's hidden prisons, the power of forgiveness, and what true freedom feels like. A16Z co-founder Ben Horowitz also joins to reflect on Shaka's journey and its lessons for leadership and growth. Let's get into it.
0:27 Speaker 01 Hey there, everybody. I am so glad to meet up with you here on the Oprah Podcast, and it is always my great hope that the conversations that you see here or listen to here can serve to open or expand the aperture of your life. And on this episode, I really hope we do that because we're exploring this question, what does it mean to be truly free? What would that look like? And more importantly, what would it feel like inside yourself for you? And consider asking yourself, what is holding you back
1:09 Speaker 01 from pure freedom? I'm here with bestselling author, Shaka Sankor. Welcome back to the tea house.
1:17 Speaker 02 I'm so excited to be here, and thanks so much for having me.
1:20 Speaker 01 10 years.
1:20 Speaker 02 10 years, our 10 year anniversary.
1:22 Speaker 01 Yeah, 10 years.
1:23 Speaker 02 Yeah.
1:24 Speaker 01 Let me tell everyone listening and watching that Shaka and I first met here 10 years ago. And as we were saying coming in, a lot of living has happened with both of us since then.
1:36 Speaker 02 Yeah.
1:37 Speaker 01 When I first met Shaka Sankor, it had been about six years since he got out of prison after serving 19 years, many of them in solitary confinement for tilling a young man when Shaka himself was just 19. It is one of my most memorable interviews ever. We talked about his troubled life that led to that fateful day. You just had an aha there.
2:00 Speaker 02 There.
2:00 Speaker 01 Yeah.
2:02 Speaker 01 What Shaka has achieved in this decade since that conversation is truly extraordinary. His book, Writing My Wrongs, became a New York Times bestseller. He landed and left a high-powered corporate job, started his own business, even collaborated with the rapper Nas on a hit song. His new book, How to Be Free, is a must-read for anybody looking to manifest their own vision of freedom. What's your advice to anyone who is stuck, needing to forgive or be forgiven? With How to Be Free, Shaka has written a workbook filled with hard-earned life lessons and practical exercises that he uses, and you can too,
2:46 Speaker 01 to liberate both body and mind. Ooh, I love that. I fell in love with my mind.
2:55 Speaker 01 I love this question of being free. So I want to dive right into it because it's your newest book, How to Be Free, How to Be Free: A Proven Guide to Escaping Life's Hidden Prisons. I saw this title and I thought, whoa. How to be free, isn't that one of the core things that we all are striving for? And what made you write this? Because 10 years ago, you wrote a book called Writing My Wrongs, which I just love that title. And How to Be Free, you've been free now for how many years?
3:31 Speaker 02 Coming up on 15 years. So it's really amazing to even think about that part of my journey after spending 19 years to now be 15 years this side of freedom. And to be able to live this experience is really what inspired the book.
3:47 Speaker 01 And you were inspired because you have conversations with other people and you realize there are many people who are...
3:55 Speaker 01 Not like you. They hadn't been to a real prison, hadn't been incarcerated behind bars, but are incarcerated in their own self-imposed bars.
4:05 Speaker 02 Yeah.
4:06 Speaker 01 Yeah.
4:06 Speaker 02 Yes, you know, it's been one of the most incredible parts of my journey is to think about, what does it even mean to be free? And obviously, I had the kind of very real experience of being physically incarcerated. But what came up for me was that I was free before I ever got out of prison. I was actually free before I even knew I was getting out of prison. But I was also incarcerated before I went in. Because I had bought into a narrative that my life could only have very limited outcomes. And so when I got out and I started.
4:34 Speaker 01 Okay, so let's start with that.
4:35 Speaker 02 Yeah.
4:36 Speaker 01 You were incarcerated before you went into prison.
4:39 Speaker 02 Absolutely.
4:40 Speaker 01 Tell us what that means.
4:41 Speaker 02 Yeah, so the mindset that I embraced, this narrative that my life can only have two outcomes. I would be dead or in jail before I was 21. And so I lived within this very limited belief about.
4:53 Speaker 01 That was its own incarceration.
4:54 Speaker 02 That was my own prison, the own hidden prison. And so I began to live my life through that lens and it produced that outcome. I ended up being that environment. And then when I had this awakening, you know, I was doing this journal and just really trying to ask this question of like, how did I end up here? And what's next for me?
5:13 Speaker 01 And this was how many years into your, into your imprisonment, into your incarceration?
5:18 Speaker 02 This was roughly about eight or nine years in. I was in solitary confinement and really coming to terms with like what my life had become. And I started journaling and just asking these hard questions. How did I end up here? And what I discovered was that all these things had happened early in my childhood, the trauma, the abuse, the violence. And most importantly was the narrative that I embraced.
5:40 Speaker 01 And also the choices that you made as a result of that narrative.
5:43 Speaker 02 Absolutely, absolutely. And that was one of the most powerful things, that if I can choose based on this negative narrative and create these negative outcomes. What would happen if I chose positive narrative and started to live my life with those outcomes in mind?
5:59 Speaker 01 Because you could really physically see that for yourself when you're journaling. And solitary confinement, you have a lot of time.
6:06 Speaker 02 Yeah, yeah.
6:07 Speaker 01 And you were able to absolutely go through the patterns that had put you exactly where you were.
6:12 Speaker 02 Absolutely.
6:13 Speaker 01 Yeah.
6:13 Speaker 02 Yeah, and it was steps. And it was steps like any other thing that you want to build out. There are steps you have to take. And I took steps that led me to prison. So I was like, what are the steps necessary to lead me out of it? And lead me up into the greatest sense of what it means to be free. And that journaling really opened up all the possibilities because I fell in love with my mind.
6:34 Speaker 01 Oh, I love that. I fell in love with my mind. And so, long before you were actually let out of the walls of the prison, you felt that you had liberated yourself within the walls of the prison. Tell us about that.
6:51 Speaker 02 Yeah, what I discovered in that in that space was that I can go wherever I wanted to go in my mind. And they could take me to places far beyond the prisons. But more importantly, what it did is it showed me that there's still possibility. You still have a life left. And if you can dream, you can actually achieve it. Like, it was really like, even though it's one of those things we hear all the time, you know, conceive it, dream it, believe it, and it'll happen. It really became a mantra for me. And I just started writing down, here's what I want to happen in my life. And I've realized that writing it down was just part of it. And I, you know, I encourage people to journal, but it's also active journaling. What are the steps that I'm going to take to make this become reality?
7:35 Speaker 01 So, active journaling, so give us an example. You would write down?
7:39 Speaker 02 So I wrote down that I wanted to finish something. Because what I learned during my journaling is I had never completed anything. I never graduated high school. I never followed up going to the military. I always started things but never finished anything. So one of the first things for me was you have to complete something. And that something was writing a book. And I gave myself a very defined timeline to do it. Thirty days, you have to write a book. And that was the action step. And what I said to myself when I wrote that down, if I finish this book in thirty days, my life can be anything that I imagine it to be. And I did it.
8:16 Speaker 01 And that's how Writing My Wrongs came.
8:19 Speaker 02 That was the beginning of my writing journey, which led to Writing My Wrongs eventually.
8:23 Speaker 01 Yes, yes. And so I want to say that I think that this book, How to Be Free: A Proven Guide to Escaping Life's Hidden Prisons, is, it's a guide.
8:36 Speaker 02 Yeah.
8:36 Speaker 01 For anybody looking to tear down their own self-imposed barriers to getting free. And you write on page four, How to Be Free, that prison, you say, prison is designed to break you. The walls, you say, the rules, the routine, it's all meant to just strip you down until you forget who you are. And what you discovered is that the most powerful prisons aren't the ones made of concrete and steel, but they're the ones that we carry with us that are built from our anger and our shame and our trauma and our self-doubt. So is that why you wanted to write this book?
9:14 Speaker 02 Absolutely. You know, on my journey, when I put Writing My Wrongs out, people would come up and share stuff with me that they said they had never shared before. A child who committed suicide, a dysfunctional marriage, a failure at job. And they would say something about having a conversation really opened them up and liberated them. And so I started just kind of interrogating this idea of like, what keeps people locked in place? And these things just kept coming back. Grief, shame, anger. And the more-
9:43 Speaker 01 Forgiveness.
9:44 Speaker 02 Forgiveness, inability to forgive.
9:46 Speaker 01 Yeah.
9:46 Speaker 02 And the more I kept coming back to that, I started to see it in people from all walks of life, which was the thing that was mind-blowing to me. Because, you know, we come with these narratives where we think we got people's, other people's lives figured out.
9:58 Speaker 01 Yeah.
9:58 Speaker 02 Oh, they're successful, so they can't have problems.
10:00 Speaker 01 Yeah.
10:00 Speaker 02 They're wealthy, they can't have problems. They're this, they're that. And then you start to talk to people and you realize we all have it. You know, we all have things that we're working through and sometimes we're not even aware that, you know, we're working through them.
10:13 Speaker 01 And that everybody is just here doing the best they know how at any given moment. So I know that forgiveness for you has become like a healing agent in your life. And you received it from, you write this in Writing My Wrongs, the godmother of the young man that you had shot and killed, and that's what landed you in prison. You also gave forgiveness to the man who killed your younger brother,
10:35 Speaker 02 Yeah.
10:36 Speaker 01 Sherrod. What's your advice to anyone who is stuck needing to forgive or be forgiven?
10:44 Speaker 02 That that part of my journey has been so profound. Because, you know, when you receive forgiveness, you forget that sometime in life, you may have to forgive someone. And it can be so complex. It's not it's not an easy thing. You know, my brother was murdered in two thousand twenty one. And it was heartbreaking because my gut reaction was all the negative things that come with losing a loved one. And then I thought about this person's soul, like what led him down that path. And it was really having empathy and compassion for his journey. Um, because I had my own experience. So there was carrying the duality of guilt while trying to grieve.
11:26 Speaker 02 And then reconciling that through what what have I been teaching in the world? Whatever I've been saying to people all along. And now it comes front and center in my own life. And I think that's the power of what this book is really about is that true freedom doesn't come without the work. You're always going to be confronted with the work. You're always going to have a thing to challenge you to to think broader about what it is that you're sharing in the world.
11:49 Speaker 01 And I think people always miss the point of forgiveness because you really do it for yourself.
11:55 Speaker 02 Absolutely.
11:56 Speaker 01 You do it to free yourself. So that you're not carrying around this ball of anger, this grudge, this need to revenge. You release it. So it doesn't mean you now want to go sit and have a meal.
12:10 Speaker 02 Right.
12:11 Speaker 01 With the man who shot your brother.
12:12 Speaker 02 Yeah.
12:12 Speaker 01 It means you're able to find some peace in it.
12:16 Speaker 02 Absolutely.
12:17 Speaker 01 Yeah.
12:17 Speaker 02 Yeah, because I mean, that was the gut reaction was the anger. You know, the gut reaction in my family, which is natural to be upset, to be heartbreaking.
12:24 Speaker 01 We want to get you.
12:25 Speaker 02 Heartbroken, yeah. And so now it's like, OK, do I want to carry that for the next twenty, thirty years? Uh, do I want to show that as, you know, as I move through life? You know, I have a young son. I have mentees. I have people who look up to me. How do how do I navigate that?
12:40 Speaker 01 Yes.
12:41 Speaker 02 You know, for me, and you know, it's a heavyweight to carry to have that level of anger, uh, just hanging over your head.
12:47 Speaker 01 So when you were seventeen, you were shot by a man named Terrence.
12:49 Speaker 02 Yeah.
12:50 Speaker 01 And I think this is so remarkable. You write about receiving a letter from Terrence thirty two years later. What does it say about the weight or the burden that he reached out all those decades later?
13:04 Speaker 02 It is one of the most powerful and complex experiences I've ever had in my life. When I first got the letter, there was a full range of emotions that went through my mind. Because I've never really saw this guy's face. That shooting was our only encounter, which was about 30 seconds. And I didn't realize that that inability to see this guy's face had haunted me all these years. And how he came about even knowing who I was.
13:30 Speaker 01 But that guy shooting you is what sent you on another path. Because that's when you went and got your own gun.
13:37 Speaker 02 Yeah, it was the cycle.
13:38 Speaker 01 Yeah.
13:39 Speaker 02 You know, and when I got that letter,
13:43 Speaker 02 you know, I bristled up, my body just tensed up with all the anger.
13:46 Speaker 01 Where were you? What was going on in your life?
13:47 Speaker 02 I was actually home. I was at home in LA. And you know, I was outside and it's beautiful, sunny. And you know, I opened the letter and I was just like, whoa. Like, and all the things, that moment came flashing back. And then I was like, I gotta see this guy's face. So I got on the computer and I looked him up because he's still in prison. And just seeing his face, like, it felt like the weight of the world came off my shoulders.
14:11 Speaker 01 Really?
14:11 Speaker 02 Because I was able to humanize this guy. And he was no longer this boogeyman that just kind of hid in the shadows of my past.
14:17 Speaker 01 So how did he find you and why did he write you?
14:19 Speaker 02 So he found me because another guy was reading my book in prison. And passed it on to him, he started reading it. And he was like, oh my God, this is the guy I shot. And here's what the outcomes of his life was as a result of that moment. And he took so much responsibility for that moment. And I still have complete agency over that decision. But I understand how he would arrive at how one incident can spiral somebody into, you know, an incident that changed their life.
14:47 Speaker 01 That's right, because that incident caused you to start carrying a weapon yourself.
14:52 Speaker 02 Yeah.
14:52 Speaker 01 And everything that resulted from that.
14:54 Speaker 02 Yeah.
14:55 Speaker 01 So is it true that you've not written him back yet?
14:58 Speaker 02 So I started writing it and then I didn't finish it. And then I put it up and I was like, you know, I don't owe him a letter. Um, you know, and I think that's one of the things about forgiveness. You know, it's not about him. It was really about me. And what I realized was like, what matters in my life today? Who are the people around me today that matter that I can forgive? And build deeper relationships with? And he wasn't one of them. Um, and, and I'm okay with that. You know, I've forgiven him and, you know, I hope for the best life outcomes for him. But I didn't feel it was necessary for me to follow through with, with writing that letter.
15:34 Speaker 01 But you had started to write a letter?
15:35 Speaker 02 I did start to write it.
15:36 Speaker 01 And what did you want to say at that time?
15:39 Speaker 02 Well, I wanted to say thank you for finally revealing your face. I thought that was really, really important, uh, part of my journey and that I appreciate.
15:47 Speaker 01 Cause you didn't even realize how haunted you were by not knowing.
15:50 Speaker 02 Yeah.
15:50 Speaker 01 Cause he really is then the boogeyman.
15:52 Speaker 02 Yeah, he's literally a ghost. He was just like a phantom. Um, and, and just to having the courage to say, I'm sorry. I imagine an environment that he's in. Cause I've been there and it's not the easiest environment to be apologetic. Uh, or to say you was wrong about something and, you know, 32 years later.
16:08 Speaker 01 Or to admit anything.
16:09 Speaker 02 Yeah. Yeah. Cause it's not even encouraged in that environment. And so I thought that was brave of him, you know? And that's, that's what I would've said. I thought that was brave step to take. And knowing that, you know, he's, he's very vulnerable to even reach out because I still have a lot of influence in that environment. And he didn't know how healed I am or where I'm at in my journey. So just the courage to say, you know, I'm gonna say I'm apologizing to this guy who can potentially do me harm. You know, I thought that was courageous.
16:35 Speaker 01 But you, you, you haven't responded to his letter, but you do say that that letter helped you in the healing process with your own mother? How?
16:43 Speaker 02 Yeah. Yeah, I actually wrote my mother a letter and it was.
16:46 Speaker 01 So he wrote you a letter and then you thought you wrote your mother?
16:48 Speaker 02 Yeah, I wrote my mother a letter and, you know, my mother and I had a very complex relationship, you know? Going back to all the things that I had written about before. And what I learned most about forgiveness.
17:00 Speaker 01 Yes, I just want to share with this audience. I'm going to bring it up because it is in, in the book. It's certainly in, in, um, writing my wrongs. That, that seminal moment for me was when you walked into the kitchen as a nine-year-old boy with your report card and your mom throws a pot of whatever she was cooking at you. And in that moment, everything changed for you, you know?
17:25 Speaker 02 One time I was coming home from school. And I was like the smart kid in the family. And so my grades was like the thing that I was most proud of. And so came home super excited to.
17:36 Speaker 01 How old are you?
17:37 Speaker 02 I'm probably in the fourth grade, so I'm assuming like eight now.
17:41 Speaker 01 Eight?
17:42 Speaker 02 I'm not sure yet, right? And I came in and she was at the kitchen sink watching dishes. And I was like, you know, Ma, I got to school on my test. And she rolled around and threw a pot with like such force that it broke the towels on the wall.
17:56 Speaker 01 But that's a life shattering moment when you think about it.
17:59 Speaker 02 Yeah, devastating.
18:00 Speaker 01 That's a life shattering moment when you think about being an eight year old or nine year old, coming home and saying, Mom, look at my grades.
18:09 Speaker 01 So you've had a volatile relationship with your mom.
18:11 Speaker 02 Absolutely.
18:12 Speaker 01 Over the years. It took her 17 years to come to visit you.
18:16 Speaker 02 Yeah.
18:16 Speaker 01 When you were incarcerated. And after you get the letter from Terrence, who shot you and sent you on a spiraling path downward, you then are moved to free yourself to write your mother.
18:32 Speaker 02 Yeah, and so when I sat down to write the letter, I thought I had forgiven my mother. You know, my mother came to see me on that visit. I was like, you know what, Ma, I forgive you. I've moved on. But what I realized is that I was holding on to this idea that my forgiveness would somehow change her, which would in turn change our relationships. And so that that little boy part of me that just wanted to be nurtured by my mother, I thought I can change that. And it wasn't until I was.
18:58 Speaker 01 Ooh, this is such a good point that you're making.
19:00 Speaker 02 Yeah.
19:00 Speaker 01 That if you're going to forgive with conditions in play.
19:04 Speaker 02 It's really not forgiveness.
19:05 Speaker 01 It's really not forgiveness.
19:06 Speaker 02 Yeah, and I learned it through a conversation with my older brother. We were talking and he just said to me, you know, I forgave Mama and then she did this again. And I forgave her. And it just struck me and I was like, whoa, I've done the same thing. I put all these conditions around it without even interrogating how she even got to become the woman that she was. And so I was like, you know, if I'm going to get to this deep sense of forgiveness, I just got to know her story. And if she's willing to go on that journey with me, the possibilities are infinite. And so we went on that journey and we spent time together. We talked deeply and my mother shared things with me that was heartbreaking.
19:50 Speaker 02 Yeah, just to think about what her young life was. And I don't think we do enough of that when it comes to our parents, right? There are heroes.
19:58 Speaker 01 Yeah, we just say, we say this term, hurt people hurt people.
20:01 Speaker 02 Yeah.
20:02 Speaker 01 But you don't realize what the hurt was like for those people.
20:05 Speaker 02 Yeah, yeah. And so with my mother, she was willing to open up. And she just shared all these things that she had went through, the abuses, the assaults on her body. And she was willing to really share that with me. And I thought it was one of the most powerful things that she could ever do. And so I wrote her a letter, just letting her know how much I appreciated her opening up in that way. And it just allowed me to see her. And it kind of reversed the kind of dynamics in our relationship where I feel more parental. I feel more like I want to protect that little girl that didn't get protected. Who became that woman that hurt her own kids. And so, you know, that's the power of like what real forgiveness is. And when you remove all the expectations that someone will become different.
20:50 Speaker 02 Or that somehow it's for them.
20:52 Speaker 01 That's true freedom.
20:53 Speaker 02 That's true freedom. And it's like, I have so much grace for her. I have so much joy whenever we're together and when we're not. I have grace and joy when it's going good and when it's not, and it's fine, you know?
21:07 Speaker 01 So that's really the meaning of unconditional.
21:10 Speaker 02 Absolutely.
21:11 Speaker 01 Meaning I'm going to forgive you, I'm going to love you regardless of what you do.
21:16 Speaker 02 Yeah, and you have to just.
21:17 Speaker 01 That's hard, though. That's hard. Chaka, that's hard.
21:20 Speaker 02 What you know why it's hard is because the hidden part of it is we still have these conditions, right? And the conditions are.
21:27 Speaker 01 I'm going to do this, but what I want is for you to change.
21:30 Speaker 02 Yeah, and if you don't change, just don't hurt me again. The reality is that the people that you forgive can possibly hurt you again. And then you have to decide, okay, do I want to go back into that door again? You know, and that's the complex things with, especially with parental relationships.
21:46 Speaker 01 Yes.
21:46 Speaker 02 Because it's just your parents, you know, or your children. And that means that old things can be brought up over and over. They can be triggering. But once I release the things, the things that used to trigger me, I'm just like, that's hurt. That ain't got nothing to do with me, you know?
22:01 Speaker 01 Well, don't you think too, when you can't. Forgive without conditions being placed upon the forgiveness, that it's really challenging to experience true joy.
22:14 Speaker 02 Absolutely, absolutely.
22:15 Speaker 01 Isn't it?
22:16 Speaker 02 Yeah, and I mean, joy is is one of the great markers of freedom.
22:20 Speaker 01 That's right.
22:20 Speaker 02 How do you really show up in your life? And, and you know, what are the things that feel pleasant in your spirit and in your being? And you can't have that if you're holding on to anger and you're holding on to shame for things that don't even no longer exist.
22:34 Speaker 01 I think that's a great line. Joy is one of the great markers of freedom.
22:37 Speaker 02 Absolutely.
22:38 Speaker 01 And I also know that you believe, and you talk about this in How to Be Free, that resilience is a spiritual principle. Explain that.
22:47 Speaker 02 Yeah, I mean, you think about how we got here. Like, we were born through a resilient effort. The biological makeup of how a sperm reaches an egg, like, there's a fight there.
22:57 Speaker 01 Yeah.
22:58 Speaker 02 Yeah, people get into this kind of comparative Olympics where they're like, well, I didn't have it as hard as you, and so I'm not as resilient as you. But I'm like, I didn't go into prison knowing I was resilient. You know, I was faced with adversity that forced me to make a decision of how do I want to live my life? Do I want to forge ahead, or do I want to just quit? And what I knew was embedded in my DNA was resistance and struggle and to overcome adversity. And we all have that. We're born with it. We, you know, sometimes we give it up. We give up agency over how we're going to take a stance on something we believe or care about. But it's so spiritual, and it's the thing about life. You know, as I just mentioned, like, you don't, you don't get to the other side of these things without having to work for it. Forgiveness, I had to work for that.
23:43 Speaker 02 You know, that, that idea that people are redeemable. The Creator said, you know what? Let's see how much you really believe that. I want to put the person who shot you right back in your face. I want to put the person who shot your brother right back in your face. What do you really believe? And that's the spiritual nature of like, really working through something that's very tough. And the, the opposite of that is I could have went right back into the anger. I could have shrunk right back into the space that didn't allow me to be happy and joyful. And that's the hidden part of other prisons.
24:14 Speaker 01 I know you believe in mentors because you are one Absolutely. to so many people. And one of the great mentors in your life is Ben Horowitz. Yes. Who is a very well-known venture capitalist in Silicon Valley, and one of the founders of the legendary firm Andreessen Horowitz. And you write about his instrumental guidance in your life. Now, some of you may know Ben is the author of two New York Times bestsellers, The Hard Thing About Hard Things and What You Do Is Who You Are. Ben is joining us via Zoom. Welcome, Ben. Hi, Ben.
24:48 Ben Horowitz? Hey, Oprah. How are you? Good to see you. Chaka.
24:51 Speaker 01 Hey, bro. So Ben, I'm going to ask you to tell the story of how you and Chaka first met. I think I have something to do with that, actually.
24:59 Ben Horowitz? You did. You did. So you were screening Belief.
25:02 Speaker 01 Yeah.
25:03 Ben Horowitz? And you screened it in Silicon Valley.
25:05 Speaker 01 Yeah, I'd done a series on religions all over the world, and I was screening it. You had been gracious enough to interview me in Silicon Valley.
25:13 Ben Horowitz? Yeah. So because I had to interview you, I was terrified, just because you're really good at interviewing. And so I thought, okay, this is, I hope she doesn't judge me. And then I got back to like, you know, maybe I could ask you a few questions about interviewing beforehand, and that would help me. And you said something that was really insightful. You said, you know, I always ask people before I interview them what their intention is, and then that they have to trust me to get that intention. She says, I'll give you an example. And the example was, you know, you said, I just had this guy on my show, Super Soul Sunday. He had tattoos, dreadlocks, big muscles. He's a real scary guy. Just got out of prison.
25:58 Ben Horowitz? And I asked him before the interview, I said, you know, I'll help you get your intention, but you have to tell me what it is. And he said, well, my intention is that, you know, people won't be judged by the very worst thing that happens in their life. That people can be redeemed. And so then you proceeded to tell about the interview. And it was a story that you just mentioned.
26:18 Speaker 01 That still makes me want to tear up. Yeah.
26:21 Ben Horowitz? And I told my wife, Felicia, who you know. And she got very excited. So she reached out to your team, got the galley for his book. And so we read the book. And then the next thing I know, she says, oh, you know, I Facebook messaged Chaka, and, you know, he's going to come over to dinner tomorrow night. And I was like, Are you crazy? Did you read that book? I was like, that guy was the prison, he's a prison gang member. And so I said, look, we set it at a restaurant. You know, we'll go to a restaurant.
26:49 Speaker 01 Don't bring him to the house, Felicia.
26:52 Ben Horowitz? We could just go home. Don't invite him to the house. So then she goes, okay, and we moved it to a restaurant. And then we meet and it was really, I'd say a little bit shocking for me because in talking to him, he actually sounded like, you know, I work with CEOs all day. He sounded like a really, really advanced CEO. Like, he knew all about like psychology, motivations, systems, how they work together, how you get to the truth. And I was like, wow, I could learn a lot from this guy about how he thinks about these things. And then actually, the other thing that was very insightful to me, or like shocking, which I really wanted to know the answer to was,
27:37 Ben Horowitz? you know, there's this thing about solitary confinement, which it's very bad. There's big movements against it because, you know, you go crazy after like two weeks in there. He was in it for seven years. And like, no question, he came out like better than when he went in. And I was so interested. I was like, how did that happen? Like, what happened? And it's actually the story of this book, which is, it's when he rewrote his own narrative. It's when he finally had the time and space to do that. And that was just so, because so much of achievement and building something great is being able to get to your own truth and be comfortable with that. And his truth was so scary and dark.
28:22 Speaker 01 I know. And to be able to use solitary confinement, that confinement, to actually explore his inner world that way, and to be truthful with himself about the results, is what's so fascinating. And what's so fascinating about the first book, Righting My Wrongs, and what's so fascinating now about How to Be Free, that you were able to really tap into what that looks and feels like, even before he was let go. You say Ben taught you an important lesson about failure. What is that?
28:55 Speaker 02 Yeah, so you know, Ben and I, we talk a lot about success. And I remember asking what does success mean? And he said to me, it's a series of smart decisions and a step by step. And I ended up asking that question again recently. And he was like, it's the same thing with failure. It's a series of steps taken in opposite direction. And I was like, whoa. Because you know, it's like we can think about the steps toward something positive and progressive. But we don't also always think about failure as it's a series of things that you also do. Failing to show up, failing to be curious, failing to follow through. All these things are steps that lead in one very clear direction. You're going to fail.
29:37 Speaker 02 And that was just, it was so mind blowing to hear that, his perspective on it.
29:41 Speaker 01 I think what's so mind blowing is that you had told Felicia, this guy's a real criminal. Don't invite him to the house. Now you guys are like best buddies. Well, thank you, Ben, for joining us. Thank you for being a part of it. Thank you.
29:57 Speaker 01 So you've been out of prison now for 15 years, as we said at the beginning of this conversation. And almost as long as you were inside prison.
30:06 Speaker 02 Yeah.
30:07 Speaker 01 And I hear you recently applied for a pardon.
30:10 Speaker 02 Yes.
30:11 Speaker 01 For the first time. What would a pardon mean for you? Now that you are already free and you're writing books about how to be free. So what would a pardon mean?
30:20 Speaker 02 You know, when I first put in the pardon, I thought it would just be a symbolic gesture.
30:25 Speaker 01 Yeah.
30:26 Speaker 02 And what I realized recently, every time that the mail comes and I'm out looking for that letter is that I've wanted it more than I had given myself permission to believe. And what it means for me is that I'm now back part of the tribe.
30:40 Speaker 02 When you have a felony on your record, you're exiled. And even when you're as successful as I've become over this last 15 years, there's still things that come up that's kind of like that slap on the hand reminder of this is who you were and this is who we'll always think you are. And, you know, when I was filling out that paperwork, I had delayed it for a long time. I was like, oh, maybe I get a lawyer to do it, et cetera. And I was like, you know what, you have to do it. And, you know, I've said, I've carved out the time to do it. Um, and so for me, it's like, just getting granted that would mean I'm back a part of the tribe.
31:16 Speaker 01 Hmm. This is a question I probably should have asked you at the beginning of this conversation because I think that for most people who think of someone who's been incarcerated and incarcerated for 19 years and incarcerated on, uh, you know, been in solitary confinement, that the moment you are released from prison, you would experience freedom in a way that we can't even imagine, you know? I still think of people that I know who are on death row, who haven't seen a moon.
31:53 Speaker 02 Yeah, yeah.
31:54 Speaker 01 And haven't seen the stars. And I would just think, wow, everything in life would just feel like freedom, freedom, freedom, freedom. And yet, when I read How to Be Free, I recognize that there's so many people who are released and are still imprisoned once they're released.
32:11 Speaker 02 Absolutely, absolutely.
32:12 Speaker 01 Yes.
32:13 Speaker 02 And, and, you know, for me, I, I still have that feeling as if I walked out the first day.
32:19 Speaker 01 You do?
32:19 Speaker 02 I marvel at life. I am so in love with life. I'm in love with the details of life. Uh, I'm fascinated by so many things. I'm curious about so many things.
32:29 Speaker 01 Anthony Ray Hinton, who wrote The Sun Does Shine, said that when he came out, rain meant so much to him, just to be able to feel the rain.
32:37 Speaker 02 Yeah, all the details, I love it. Uh, and, and I think it's part of, you know, when I wrote this book, I want people to go back into that feeling. Because I think we get caught up in the mundane of life and we forget about the beauty of nature. We forget about the beauty of a casual walk with a friend. We forget about like really experiencing food, not just for nourishment, but as a real experience. Uh, we forget about like what joy is, you know? It's, um, going back to Ben, like we have these moments where we're just like, dude, let's grab this vinyl and this is, listen to music and talk about the details of art that went into creating this piece of, of work. And so. To me, it's like every day is a day of freedom.
33:16 Speaker 01 So for someone who's listening to us today, watching us today, and they want to begin the journey for themselves to be free, they should do what?
33:24 Speaker 02 They should start journaling. I would say that's my number one out of everything else. Like meditation is incredible, practicing mindfulness. Those things take a little bit of work. But journaling is something that we all have access to, even with technology now.
33:38 Speaker 01 Like if Donnie just sat down and looked at and asked the question, how did I get here?
33:43 Speaker 02 Yes.
33:43 Speaker 01 It's the same question that you asked. You were in solitary confinement asking it. But asking the question, y'all, wherever you are in your life, of how did I get here? And being able to relate to your own story, like choice by choice by choice that put you here. I mean, allows you to see, look at all you've endured.
34:03 Speaker 02 Yeah. And even keeping that gratitude journal.
34:05 Speaker 01 Yes, I believe in that.
34:07 Speaker 02 What is the most magic thing that's happened to me today? And that's something that keeps me so grounded and it helps me get through like those tough moments, right? So when I was going through everything with my brother, I was like, I was just writing, you know? I was writing letters to the perpetrator. I was just writing out my thoughts, like, how do I really feel? Like, what's living inside my being right now? And then what am I thankful for? You know, what is the, what is the thing that brought me a sense of joy today?
34:33 Speaker 01 Yeah.
34:33 Speaker 02 You know, what does that thing look like? The payoff for that is so great, you know, especially when you come back days later. Because you move through life, you can start forgetting about like, how many things did I do this week that was amazing? It's easy to just move through those things and forget about them. But I try to take it all in.
34:49 Speaker 01 Oh, I do too. And I write down the Godwinks because you really forget the things that, you know, the things that other people call coincidences or serendipity or whatever, where you just go like, wow, how did that thing happen?
35:01 Speaker 02 Yeah.
35:01 Speaker 01 If you don't write it down, you'll forget it.
35:03 Speaker 02 Yeah, absolutely.
35:04 Speaker 01 Absolutely.
35:05 Speaker 02 Absolutely.
35:06 Speaker 01 Thank you for this book.
35:07 Speaker 02 Thank you so much for having me.
35:07 Speaker 01 Thank you, Shaka, and thank you for being here today. Thank you, Ben. Thank you for zooming in with us. Shaka's book is How to Be Free, and it's available September 9th, wherever books are sold. To all of you listening and watching, I appreciate you sharing your valuable time with us here. And let's meet up again next week. Go well, everybody. You can subscribe to the Oprah Podcast on YouTube and follow us on Spotify, Apple Podcasts, or wherever you listen. I'll see you next week. Thanks, everybody.
35:38 Speaker 00 Thanks for listening to the A16Z Podcast. If you enjoyed the episode, let us know by leaving a review at ratethispodcast.com/a16z. We've got more great conversations coming your way. See you next time.
35:53 Speaker 00 This information is for educational purposes only and is not a recommendation to buy, hold, or sell any investment or financial product. This podcast has been produced by a third party and may include paid promotional advertisements, other company references, and individuals unaffiliated with A16Z. Such advertisements, companies, and individuals are not endorsed by A-H Capital Management, LLC, A16Z, or any of its affiliates. Information is from sources deemed reliable on the date of publication, but A16Z does not guarantee its accuracy.
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