The a16z Show - How to Be Free: Shaka Senghor, Oprah Winfrey, Ben Horowitz

Episode Date: September 5, 2025

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 r...esilience 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.Timecodes: 0:00 Introduction 1:30 Shaka’s Journey: From Prison to Freedom4:10 The Power of Narrative and Mindset6:10 Active Journaling & Writing My Wrongs8:45 Escaping Life’s Hidden Prisons10:00 The Role of Forgiveness16:40 Healing Family Relationships21:00 Unconditional Forgiveness & True Freedom22:40 Resilience as a Spiritual Principle24:15 Mentorship & Meeting Ben Horowitz28:55 Lessons on Success and Failure30:20 The Meaning of a Pardon31:50 Life After Prison: Finding Joy in Freedom32:30 Advice for Listeners: How to Begin Your Own Journey35:15 Closing Thoughts Resources: Find Shaka on X: https://x.com/ShakaSenghoFind Ben on X: https://x.com/bhorowitzFind Oprah on Instagram: https://www.instagram.com/oprahpodcast/Listen to the full podcast:https://open.spotify.com/show/0tEVrfNp92a7lbjDe6GMLIhttps://podcasts.apple.com/us/podcast/the-oprah-podcast/id1782960381 Stay Updated: Let us know what you think: https://ratethispodcast.com/a16zFind a16z on Twitter: https://twitter.com/a16zFind a16z on LinkedIn: https://www.linkedin.com/company/a16zSubscribe on your favorite podcast app: https://a16z.simplecast.com/Follow our host: https://x.com/eriktorenbergPlease note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Stay Updated:Find a16z on YouTube: YouTubeFind a16z on XFind a16z on LinkedInListen to the a16z Show on SpotifyListen to the a16z Show on Apple PodcastsFollow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Starting point is 00:00:01 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. 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.
Starting point is 00:00:44 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, more importantly, what would it feel like? inside yourself for you. And consider asking yourself, what is holding you back from pure freedom? I'm here with best-selling author, Shaka Sankor.
Starting point is 00:01:16 Welcome back to the Tea House. I'm so excited to be here, and thanks so much for having me. Ten years. Ten years, our 10-year anniversary. It's incredible. Yeah. Let me tell everyone listening and watching that Shaka and I first met here 10 years ago,
Starting point is 00:01:29 and as we were saying coming in, A lot of living has happened with both of us since then. Yeah. When I first met Shaka Sincor, it had been about six years since he got out of prison after serving 19 years, many of them in solitary confinement, for killing a young man when Shaka himself was just 19. It is one of my most memorable interviews ever.
Starting point is 00:01:54 We talked about his trouble life that led to that fateful day. You just had an aha there. Yeah. Yeah. Yeah. 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.
Starting point is 00:02:21 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 to liberate both body and mind. Ooh, I love that. I fell in love with my mind. 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?
Starting point is 00:03:14 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 loved that title. And how to be free. You've been free now for how many years? Coming up on 15 years. So it's really amazing to even think about that part of my journey
Starting point is 00:03:37 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. And you were inspired because you have conversations with other people and you realize there are many people who are 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.
Starting point is 00:04:05 Yeah. Yeah. Yeah. 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.
Starting point is 00:04:21 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... Okay, so let's start with that. Yeah. You were incarcerated before you went into prison. Absolutely.
Starting point is 00:04:40 Tell us what that means. 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... That was its own incarceration. That was my own prison. all 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
Starting point is 00:05:07 journal and just really trying to ask this question of like, how did I end up here? And what's next for me? And this was how many years into your imprisonment and into your incarceration? 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 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,
Starting point is 00:05:37 and most importantly was the narrative that I embrace. And also the choices that you made as a result of that narrative. Absolutely, absolutely. And that was one of the most powerful things is that if I can choose based on this negative narrative and create these negative outcomes, what would happen if I chose positive narrative?
Starting point is 00:05:56 and started to live my life with those outcomes in mind. Because you could really physically see that for yourself when you're journaling and solitary confinement. You have a lot of time. Yeah, yeah. And you were able to absolutely go through the patterns that had put you exactly where you were. Absolutely.
Starting point is 00:06:13 Yeah. 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 goal? greatest sense of what it means to be free. And that journaling really opened up all the possibilities
Starting point is 00:06:31 because I fell in love with my mind. 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. Yeah, what I discovered 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 happened, it really became a mantra for me. And I just started writing down, here's what I
Starting point is 00:07:22 want to happen in my life. And I've realized that writing it down was just part of it. of it. And 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? So active journaling, so give us an example. You would write down. 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.
Starting point is 00:07:59 And I gave myself a very defined timeline to do it. 30 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 finished this book in 30 days, my life can be anything that I imagine it to be. And I did it. And that's how writing my wrongs came.
Starting point is 00:08:19 That was the beginning of my writing journey, which led to writing my wrongs. Yes, 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 a guide. Yeah. For anybody looking to tear down their own self-imposed barriers to getting free,
Starting point is 00:08:42 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?
Starting point is 00:09:14 Absolutely. You know, on my journey, when I put writing my wrongs, 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 forgiveness.
Starting point is 00:09:44 And forgiveness. And the inability to forgive. Yeah. 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, oh, they're successful,
Starting point is 00:09:59 so they can't have problems. Yeah. They're wealthy. They can't have problems. They're this, they're that. And then you started to talk to people, and you realize we all have it. You know, we all have things that we're working through.
Starting point is 00:10:10 And sometimes we're not even aware that, you know, we're working through them. 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 of God, mother 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
Starting point is 00:10:33 who killed your younger brother, Sharad. What's your advice to anyone who is stuck needing to forgive or be forgiven? 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 an easy thing. You know, my brother was murdered in 2021. And it was heartbreaking because my gut reaction
Starting point is 00:11:08 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 because I had my own experience. And so there was carrying the duality of guilt while trying to grieve and then reconciling that through what have I been teaching in the world. What I've been saying to people all along?
Starting point is 00:11:32 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 think broader about what it is that you're sharing in the world. And I think people always miss the point of forgiveness because you really do it for yourself. Absolutely. 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.
Starting point is 00:12:07 So it doesn't mean you now want to go sit and have a meal with the man who shot your brother. It means you're able to find some peace in it. Absolutely. Yeah. Yeah, because, I mean, that was the gut reaction, was the, the anger. You know, the gut reaction of my family, which is natural to be upset, to be heartbreaking. We want to get you. Heartbroken, yeah. And so now it's like, okay, do I want to carry that for the next 20, 30 years? Do I want to show that as, you know, as I moved through
Starting point is 00:12:34 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? You know, for me, and, you know, it's a heavy weight to carry to have that level of anger just hanging over your head. So when you were 17, you were shot by a man named Terrence. Yeah. And I think this is so remarkable. You write about receiving a letter from Terrant 32 years later. What does it say about the weight or the burden that he reached out all those decades later?
Starting point is 00:13:04 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. But that guy shooting you is what sent you on another path, because that's when you went and got your own gun.
Starting point is 00:13:37 Yeah. It was the cycle. Yeah. You know, and when I got that letter, you know, I bristled up. My body just tinsed up with all the- Where were you? What was going on in your life? I was actually home.
Starting point is 00:13:48 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 in 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. Really? 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. So how did he find you and why did he write you? So he found me because another
Starting point is 00:14:21 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, an incident that changed their life. That's right, because that incident caused you to start carrying a weapon yourself and everything that resulted from that. Yeah.
Starting point is 00:14:55 So is it true that you've not written him back yet? 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. 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't forgive and build deeper
Starting point is 00:15:20 relationships with? And he wasn't one of them. 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 writing that letter. But you had started to write a letter. I did start to write it. And what did you want to say at that time? Well, I wanted to say thank you for finally revealing your face, I thought that was really, really important part of my journey and that I appreciate him. Because you didn't even realize how haunted you were by not knowing. Yeah. Because he really is then the boogeyman.
Starting point is 00:15:52 Yeah, it's really a ghost. It was just like a phantom. And just to have the courage to say, I'm sorry, I imagine an environment that he's in, because I've been there, it's not the easiest environment to be apologetic or to say you was wrong about something. Yeah. And, you know, 32 years later. Or you admit anything.
Starting point is 00:16:09 Yeah. Yeah, because it's not even encouraged in that environment. And so I thought that was brave of him, you know, and that's what I would have said. I thought that was brave step to take. And knowing that, you know, 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 my journey. So just the courage to say, you know, I'm going to say I'm apologize to this guy who can potentially do me harm. You know, I thought that was courageous.
Starting point is 00:16:35 But you haven't responded to his letter, but you do say that that letter helped you in the healing process with your own. own mother. How? Yeah. Yeah, I actually wrote my mother a letter. And it was... So he wrote you a letter and then you thought you write your mother. Yeah, I wrote my mother 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 is grace. Yes, I just want to share with this audience. I'm going to bring it up because it is in the book, it's certainly in writing my wrongs, that that seminal
Starting point is 00:17:10 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? One time I was coming home from school. I was like the smart kid and a family. And so my grades was like the thing that I was most proud of. And so came home super excited to... How old are you? I'm probably in a fourth grade. I'm assuming like eight now. I'm not sure yet. And I came in and she was at the kitchen sink watching this.
Starting point is 00:17:46 And I was like, you know, Ma, I got this score on my test. And she rolled around and threw a pot with like such force that it broke the towels on the wall. That's a life-shattering moment when you think about it. Devastating. 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. So you've had a volatile relationship with your mom over the years. It took her 17 years to come to visit you when you were incarcerated.
Starting point is 00:18:18 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. 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? Mom, I forgive you. I've moved on.
Starting point is 00:18:43 Well, 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 little boy part of me that just wanted to be nurtured by my mother, I thought I could change that. And it wasn't a child. This is such a good point that you're making.
Starting point is 00:19:00 Yeah. That if you're going to forgive with conditions in play, it's really not forgiveness. It's really not forgiveness. 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.
Starting point is 00:19:16 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, it was heartbreaking. Yeah, just to think about what her young life was.
Starting point is 00:19:53 And I don't think we do enough of that when it comes to our parents, right? There are heroes. Yeah, we just say, we say this term, hurt people, hurt people, but you don't realize what the hurt was like for those people. Yeah, yeah. And so when 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.
Starting point is 00:20:14 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 to let her just letting her know how much I appreciated her 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.
Starting point is 00:20:40 And so, you know, that's the power of, like, what real forgiveness is. And will you remove all the expectations that someone will become different or that somehow it's for them? That's true freedom. 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.
Starting point is 00:21:06 So that's really the meaning of unconditional. Absolutely. Meaning I'm going to forgive you, I'm going to love you, regardless of what you do. And you have to just say. That's hard, though. That's hard, chaga. 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...
Starting point is 00:21:26 I'm going to do this, but what I want is for you to change. 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. Yes. Because it's just your parents, you know, or your children.
Starting point is 00:21:49 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 anything to do with me, you know? Well, don't you think, too, when you can't forgive without conditions, being placed upon the forgiveness, that it's really challenging
Starting point is 00:22:11 to experience true joy. Absolutely. Absolutely. Isn't it? Yeah, and I mean, joy is one of the great markers of freedom. That's right. How do you really show up in your life? And, you know, what are the things that feel pleasant
Starting point is 00:22:25 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. I think that's a great line. Joy is one of the great markers. of freedom. Absolutely. 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. 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,
Starting point is 00:22:56 like, there's a fight there. 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. 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.
Starting point is 00:23:21 And then 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 get to the other side of these things without having to work for it. Forgiveness, I had to work for that. You know, that idea that people are redeemable, the creator said, you know what, let's see how much you really believe that.
Starting point is 00:23:50 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 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 the prisons. I know you believe in mentors because you are one to so many people.
Starting point is 00:24:18 And one of the great mentors in your life has Ben Horowitz. Yes. Who is a very well-known venture capitalist in Silicon Valley and one of the founders of the legendary farm, Andresen 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.
Starting point is 00:24:44 Ben is joining us via Zoom. Welcome. Hi, Ben. Hey, Oprah. How are you? Good to see you, Chaka. Hey, bro. So, Ben, I'm going to ask you to tell the story of how you in Chaka first met.
Starting point is 00:24:57 I think I have something to do with that, actually. You did. You did. So you were screening belief. Yeah. And you screened it in Silicon Valley. Yeah, I've 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.
Starting point is 00:25:13 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 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.
Starting point is 00:25:45 Jesus, 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. I just got out of prison. 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.
Starting point is 00:26:03 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. Yeah. And so then you proceeded to tell about the interview, and it was a story that you just mentioned. That still makes me want to tear up. Yeah. And I told my wife, Felicia, who you know,
Starting point is 00:26:23 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 message Shaka, and, you know,
Starting point is 00:26:36 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 reset it at a restroom.
Starting point is 00:26:48 You know, we'll go to a restaurant. Don't bring him to the house, 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 worked 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
Starting point is 00:27:22 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, you know, there's this thing about solitary confinement, which is very bad. There's big movements against it because, you know, you go crazy after like two weeks from there. He was in it for seven years. And like, no question. He's, 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
Starting point is 00:28:11 of achievement and building something great is being able to get to your own truth and be comfortable with that. His truth was so scary and dark. 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 result is what's so fascinating and what's so fascinating about the first book, writing 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. Right. You say Ben taught you an important lesson about failure.
Starting point is 00:28:54 What is that? 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 taking an opposite direction.
Starting point is 00:29:14 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. Felling to show up. Felling to be curious. Felling to follow through. All these things are steps that lead in one very clear direction.
Starting point is 00:29:35 You're going to fail. And that was just, it was so mind-blowing to hear that his perspective on it. I think what's so mind-blowing is that you told Felicia, this guy's a real criminal. Don't invite him to the house. Yeah. And now you guys are like best. buddies. Well, thank you, Ben, for joining us. Thank you for being a part of it. Thank you. Thank you. So you've been out of prison now for 15 years, as we said at the beginning of this
Starting point is 00:30:02 conversation, and almost as long as you were inside prison. Yeah. Yeah. And I hear you recently applied for a pardon. Yes. 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? You know, when I first put in the pardon, I thought it would just be a symbolic gesture. Yeah. And what I realized recently,
Starting point is 00:30:28 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. When you have a felony on your record, you're exile. And even when you're as successful as I've become over this last 15 years,
Starting point is 00:30:49 there's still things that come up that's kind of like that. Slap on a hand reminder of this is who you were and this is who will 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.
Starting point is 00:31:04 And I was like, you know what, you have to do it. And, you know, I've sat, I've carved out the time to do it. And so for me, it's like just getting granted that would mean I'm back a part of the tribe. 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, you know, been in solitary confinement,
Starting point is 00:31:37 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. Yeah, yeah. 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. Absolutely.
Starting point is 00:32:12 Absolutely. Yes. And, you know, for me, I still have that feeling as if I walked out the first day. You do? I marvel at life. I am so in love with life. I'm in love with the details of life. I'm fascinated by so many things.
Starting point is 00:32:27 I'm curious about so many things. 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. All the details. I love it. And I think it's part of, you know, when I wrote this book, because I want people to go back. back into that feeling. Because I think we get caught up in the mundane of life and we forget about the beauty of nature.
Starting point is 00:32:49 We forget about the beauty of a casual walk with a friend. We forget about really experiencing food, not just for nourishment, but as a real experience. We forget about what joy is, you know. It's going back to Ben, like, we have these moments where we're just like, do, let's grab this vinyl and listen to music and talk about the details of art that went into creating this piece of work.
Starting point is 00:33:13 And so to me, it's like every day is a day of freedom. 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? They should start journaling. I would say that's my number one out of everything else. Like meditation is incredible, practice in mindfulness. Those things take a little bit of work.
Starting point is 00:33:34 But journaling is something that we all have access to, even with technology. Like if Donnie just sat down and looked at and asked the question, how did I get here? Yes. 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,
Starting point is 00:33:51 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. Yeah, yeah. And even keeping that gratitude journal,
Starting point is 00:34:05 you know, like 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.
Starting point is 00:34:24 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 thing that brought me a sense of joy today? Yeah. You know, what does that thing look like? The payoff of that is so great, you know, especially when you come back days later,
Starting point is 00:34:39 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. Oh, I do too, and I write down the Godwinks, because you really forget the things that other people call coincidences or serendipity or whatever, where you just go, like, wow, how did that thing happen? Yeah.
Starting point is 00:35:01 If you don't write it down, you'll forget it. Yeah, absolutely. Absolutely. Absolutely. Thank you for this book. Thank you. Thank you, Shaka. and thank you for being here today.
Starting point is 00:35:10 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.
Starting point is 00:35:26 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. Thanks for listening to the A16 podcast. If you enjoy the episode, let us know by leaving a review at rate thispodcast.com
Starting point is 00:35:45 slash a16Z. We've got more great conversations coming your way. See you next time. 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 pay 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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