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"He's the self-proclaimed "#1 S--- Starter" who gets in the rooms with lawmakers and forces the difficult conversations."
How does a man facing a life sentence, labeled an "inmate" by the system, redefine his identity and build a legacy dedicated to helping others?
My guest today, Oswald Newbold (co-author of Breaking Chains, Building Futures), did exactly that. After 25 years inside, he joins me to expose the hard truth the system intentionally ignores: they focus all their data on the 60% who fail (recidivism) but refuse to study the success formula of the 40% who win.
This is a raw, faith-fueled conversation about rejecting the labels the world puts on you, finding your God-given purpose even in the chaos, and building a platform of authority founded on your story. This isn't just about prison reform; this is about personal transformation.
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Marcus Hart (00:00.808)
Oswald, it's an honor to have you in the trenches with me today. Your story is a testament to the human spirit since the life of 20, growing up with the chaos of addiction. And now you're here as an author in a force for change. And this is the core issue for so many leaders listening right now. They have the same type of powerful story. So, you know, take us back down memory lane, you know, and let us know, you know, how you got to where you are now.
Oswald Newbold (00:29.42)
well, how far back do you want me to go? I guess I should ask.
Marcus Hart (00:32.526)
Hey, you don't have to go as far as you like.
Oswald Newbold (00:36.978)
You know, just a delicate dance and in the book, Breaking Chains, Building Futures, I spoke about it. I started back from when I was six years old. So I'm a kid that were born to teen parents. My mother and father young, so they still trying to learn life. Now they have a child to raise. I grew up, I started out in the housing projects down in South Florida area in Palm Beach County. River Beach was right outside of.
which is right outside of West Palm Beach. And to give that context, I guess I could say that what Compton is to LA, what Ferguson is to St. Louis, River area beach is to West Palm Beach to give us its context. And yeah. So I think people are kind of get where we coming from. But yeah, I grew up there, but I did have a loving family. They was doing their best. But I'm one of them kids that
Marcus Hart (01:17.895)
yeah.
Oswald Newbold (01:33.394)
came up through the, I'm a teenager in the eighties, that crack cocaine era come through America. It get the best of some adults, but then you see younger people wanna get in the streets or try to get in the streets. life just went crazy from now. I mean, out of two, you're young, you think you know everything in life and have it all figured out only to come and learn that, hey, when I was 15, I thought I knew everything and I didn't know as much as I thought I
Then you turn 20, you realize, wow, I really didn't know as much. Then you turn 25 and keep going. Every day is learning. looking back, that struggle for me, so I guess to give things a little context, I know what it's like to have your loved ones get caught in the cycle of addiction. And what I didn't realize, it made me angry. It made me angry. But I thought I was angry. Well,
I felt that I was angry, really I was more hurt than angry. I just didn't know how to process that emotion as you was, I was young and I was like, man, forget that. I just take care of myself. I do whatever I have to do. But going to your own devices as a teenager, you know, we don't make all the best decisions in that young life. And just fast forward bad attitude, all that even would lead to me having a stint going through the justice system. The state of Florida gave me a good little vacation.
And it wasn't no holiday in a Hyatt either, but yeah, I walked that journey and it took me 25 years, one month, 13 days to walk that journey. And I always share with people, I'm thankful to even be here to speak to you right now because in Florida, they took parole off the books back in the year of 1983. So when you get sent...
Marcus Hart (03:27.341)
Wow.
Oswald Newbold (03:28.05)
When you get sentenced to life in prison in Florida, essentially, I always say it and the judge don't pay, basically say you will be in a pine box when you leave prison. That's how I put that. So, So just thankfully staying in the law library, you know, family going broke with lawyers. I was able to get the life sentences off of me. And then the sentence that I received was a 40 and a 15 year sentence running consecutive under the old system. That's what took me that long to do.
but I'm thankful to be here. And I always said I had gave the guys my word, cause I stayed in the law library. I fought all the way to the end. And yeah, I all the way to the end, man. I had like three weeks left. Okay, y'all owe me some game time. I want that too. Like I'll just, I just wanted it. But I gave the guys my word that I wasn't going to forget about them when I get out and whatever I had to do with the false fight in the system, trying to make things better.
That's what I come out here and do. like, even me sitting here talking to you is just me delivering on my word that I gave people that I was going to come out here and try to make a positive difference in that space. So thank you Marcus for having me on. So hopefully that give us a little springboard. That's my backdrop. Yeah.
Marcus Hart (04:48.098)
You know, that's definitely man, impressive and it's inspiring and very empowering. And just to hear how the state of Florida has changed since the time and you was able to find a way to advocate on your behalf and not just get lost in that system. It is very hard, know, like man, I get praises of God too, you know, just for you, know, being here, you know.
Yeah. There's so many that still behind bars who's, you know, who has no clue where to start when it comes to like, you know, fighting back and getting back their freedom. so, you know, I want to build a little bit, you know, there's three core steps to architecting a platform authority and, and, you have to your flag and your story has several different lessons in it, you know, but you have to choose the one heel that you would die on.
Oswald Newbold (05:26.098)
Yeah.
Marcus Hart (05:43.694)
You can't be an expert on resilience. That's too broad. You have to be an expert on a specific solution. So how did you plant your flag in the side with specific part of that massive system you were going to dominate? No.
Oswald Newbold (05:56.925)
Wow, that's a simple but complex question right there. So when you ask me why I plant my flag, why you mean in like what made me choose the industry I'm in or what principle I stand on, give me a little clarity so that I could go ahead and give you the best answer.
Marcus Hart (06:01.517)
Yeah.
Marcus Hart (06:15.5)
Yeah. So being defined as an inmate to a conflict mediator and a criminal justice reformer, that's a powerful shift in itself. know, where did you, where did you plant your flag and decided like, you no longer I'm an inmate, but I can still use part of that, you know, to help me be who I am now.
Oswald Newbold (06:37.714)
Oh, well, they gave me the title of inmate. I never accepted the title of inmate, right? So, cause what I already know, even though we may be in a prisoner uniform, even in the prison, they could have took us out of that uniform and put a suit on us. So that title at the end of the day, I knew I was a man, whether I was in prison, whether I'm out here in the suit, whether I'm in swimming trunks out at the beach, I know I'm a man. So I never lost my title as a man.
And that's why I just carry myself that way. And I just accept that, life choices got me where I'm at. Just moving forward, I'm going to make better choices so I don't give these people back my life. So they could call me an inmate, so they could treat me like an inmate. And I got to follow their instructions. So I think just me staying true to being a man helped me just get to this moment right here.
Marcus Hart (07:33.177)
I agree. And that becomes part of your authority, you know, when you can just, you know, bring it back to that realization and, you know, develop a framework behind that. And the intellectual property itself is this outside of your head, you know, all of the things that you bring to the table and, you know, the concrete proof, you know, that makes your authority nonnegotiable. And your new book, The Breaking Chains, Building Futures, that's a perfect example of this.
And from what I understand about it, it's not just a story, it's more of a strategic asset. So why was it so critical for you to forge your experience into a tangible asset like the book instead of just continuing to tell your story?
Oswald Newbold (08:16.306)
Well, actually, I'm thankful to Dr. Stanley Andresi for bringing this together because he actually asked me, well, just to give a little context to the book, they was asking Dr. Andresi to tell like success stories from people who've been through P2P. And he felt that it wasn't right for him to tell our story. He felt that the individuals need to tell their own stories. So I decided to go in with that, with the collection of authors and tell my story.
And what we were focusing on is the role of education and mentorship, how it has played a role in your success. And that made me go into something that I hadn't really gave voice to about going to my experience all the way back to elementary school. now I'll let the readers, you have to get the book to really read my story. But what I will say to you is,
I went through a training and they said, your life is your story and no one else has the right to tell it. So if we want for our story to be told, we have to have the courage to tell it, even the good, bad and ugly of it. Right? So then I realized that, that is it. And believe it or not, intellectual properties is where I want to hang my hat anyway. Right now I got about.
eight, maybe eight, eight and a half books that the rough draft in there, everything from inspirational books to work books. My family is so mad at me right now because I haven't published them yet. So this is like putting that fire under me to go forward with the intellectual property. Yes.
Marcus Hart (10:01.186)
Yeah, I think you're really doing it the right way though, you know, by coming out like this and, you know, it's all about positioning and that's exactly what you're doing, brother. you know, you create an impact along the way and your reputation as well as a number one SH hockey stick starter. That tells me you ain't whispering to nobody, you know? And so how do you strategically amplify
your message to those lawmakers, to those change makers and the people who need your story to be forced to pay attention.
Oswald Newbold (10:37.362)
But those of you who listening out there, I won't use the word they use, but they call me the crap starter around where I'm at. And what it is is I say in the room what other people want to say, but they don't have the courage to say it. So there'll be a lot of mumbling and grumbling and sidewalk talk, but we're not going to get anywhere mumbling and grumbling to each other. So when we're in them rooms, if we're going to make change, we have to have a difficult conversation.
What I have learned about that fight is how to use diplomacy when in there fighting. In there, because sometimes we get in there and we just pointing fingers and we just venting. So I strive to be articulate. I strive to have my facts and my data because it's two sides to data. Most people get the data for what favors them. And most times through the criminal justice system, they pull the data that's negative. Like, for instance, Marcus, let's say recidivism.
First of all, how they count recidivism, different places count in different ways. Some count it when you catch a new charge. They don't want to count a technical violation, but I'm like, if a guy get a technical violation, they send him back for eight years. That's a whole new sentence right there. I don't know what y'all talking about. But hypothetically, let's say that, let's just hypothetically say six out of 10 people go back to jail or prison. They focus on the six. We've been tracking the six for decades.
the negative. What are the four doing that led to their success? We need to do more of what the four is doing and duplicate that and that would impact the six. We don't never want to talk about the four. You are not a part of the four. You are not a four. They don't want to talk about us. They're going to talk about that six all day. So when we get in there, it's also bringing to the forefront those impacted by this need to have a voice.
Marcus Hart (12:20.301)
Yeah.
Oswald Newbold (12:30.97)
not be a token piece in there. I'm not a token piece for anybody. You're not gonna bring me in just to say, we got somebody justice impacted. No, no, no, no, no, no. I'm not gonna sit in the table and sit silent. They have to get somebody else to tap dance. I'm not a tap dancer. But when I'm in there and I strive to have an open mind with it, you strive to make a win-win situation, even though we know that it's already a lot of laws are biased and they target certain communities.
But to get in there, I get in there and fight. I just get in there and I get in there fight. And I notice how money changes some people where when people get like funding or they don't wanna step on toes. We got all the passion when we broke, but when we get the money, when we get the money, we don't wanna step on toes. But I don't want no money from you if...
I can't do what I'm doing. You know what I'm doing. So those who gonna give me a couple of coins, they gonna have to know what I'm doing upfront to be able to move like that. I guess I could still, I'm still got the voice cause I don't, I got all of the, the willpower, but I don't have the funding, but that don't stop me from fighting. Cause I do get to see that many tables where they do listen and I use my voice wisely. I don't squander it away because it's not just about me.
anybody impacted by the system, whether they out or still in, we've been for the voices of those who don't have the courage. So I use it wisely. And yeah, and I don't be quiet. I be quiet in the beginning and I let people commit to their chain of thought. But once I crank up, boy, that sharp fin come up out the water. It's on.
Marcus Hart (14:17.494)
I like that. To your point too, the four versus the six, sometimes it do feel like it's by design and then they do a lot of lip service and like you said, they'll take one of us and put us in front of people and expect us to be that token, be that one that you brag about but don't.
copy the formula. There's a formula that most of us have and it's that grit, it's that urge to be resilient and to be willing to not stop fighting. And you exemplify that, that you got the want to stop fighting and just do it according to how someone else says to do it.
We not built to be following some template that has proven not to work. I think if you're advocating the way you are and you say you're getting some people to listen, that's huge, man. That's real, really huge. at some point, yeah, it's a fight. It's a fight. Yeah, it's a big engine. It's a big engine that you're fighting against.
Oswald Newbold (15:22.684)
Yeah.
Oswald Newbold (15:36.666)
It's a fight though, Marcus. It's a fight, Marcus. Yeah.
Marcus Hart (15:45.999)
And that's the part that most people forget. It ain't just the alderman, it ain't just the mayor, it ain't just the chief of police, it ain't just the probation office. It's all of it. Yeah, it's a system.
Oswald Newbold (15:59.187)
It's system, it's systemic. so what I'm striving to do too is pull my brothers and sisters that's impacted by the system, even the ones who get into the data, we need to look at the data that's not being collected. And that's the positive side, because we always pull the negative side. We need to look for those positive outcomes and duplicate more of that, or we need to talk about what's not being talked about. One last example real quick.
the classroom to prison pipeline. They talk about that. So they give this standardized test and based on these test scores dictates how many jails and prison they gonna build 10, 15, 20 years from now. However, thing works. If you got a sophisticated enough program or indicators to know how many jails or prisons to build, that means you also know what that child needs to be able to bring them up so that they don't.
Marcus Hart (16:33.197)
Yeah.
Oswald Newbold (16:57.478)
need to be somebody, won't be somebody that go to jail. You won't talk about what the child needs that's going to prevent them from going. So guess what? You want the benefit. We benefit off of other people's hardships in life. That's how it is. And so that in itself is it's up to us to say, hey, OK, you're right. When a child is behind and they just get behind every year to a point, they give up and maybe the options are low for income and they might get into crime.
But guess what? If we know that, we know what that child need and why wasn't that child given what they needed to prevent that? That's the question, Rockwell. So the classroom to prison pipeline talk is just going, but nobody is fighting about, okay, if we know that that's what's gonna happen, why are we not doing any preventative measures then? Or counteracting right there. So I think that's where...
Marcus Hart (17:36.878)
Yeah.
Marcus Hart (17:51.201)
Exactly.
Yeah.
Oswald Newbold (17:54.899)
the voices of people like me and you and those impacted by the system come in because we don't want to see the next Marcus or Oswald having to talk about letting them have a podcast about something else. They shouldn't have to have this talk like this. They should be talking about some other great things in life because Os and Marcus got out there and fought it and they helped them out and that person didn't have to go down that path.
Marcus Hart (18:15.736)
Yeah.
Oswald Newbold (18:24.752)
So that's just what I'm thinking in my mind. Yes.
Marcus Hart (18:28.91)
Man, that's very noble of you to say that like, you know, it's all about capturing those who's coming behind us and so that they don't, you know, make those same mistakes. you know, which, like you said, it's prison, a pipeline. That's how it's been historically for a while now. And there's enough historical data to say, okay, let's redirect this person this way. Let's take this student and put them over here.
It's there, you know, so there's no more excuses for a lot of these people in these positions to keep on giving us the same song and rocking us to sleep slowly at the same time. So yeah, man, at what point did you just decide to say, you I got myself through, you know, but it's time to pick others up and...
and start building the futures of other people.
Oswald Newbold (19:28.102)
Actually, I started building people before I came home. I was doing it still behind the gate. And I tell people that I didn't discover my gift. Other people recognized my gift and they had to make me believe in my gift. And once I did that, I was pointing to people before I even came home. So it was just like secondhand nature once I came home. I mean, I remember times of when I was going out to the rec yard to get me some reg, you know, go to work out.
Marcus Hart (19:34.062)
Mm-hmm.
Oswald Newbold (19:58.065)
and I end up walking the whole yard with a guy just walking the track with him. Like he processing and unpacking a lot and it means something to him. It set their life on a different track. And I don't think much of it, but I'm actually seeing the results of pointing to people. So it started from in, I just didn't know how I was going to be able to carry it out out here. So when I got out, it was all about survival. I need a job. got bills.
So I was there and the person who's my supervisor, now that's my boss, he saw what I was doing in the community for free after I got off my nine to five job. And he like, as you could get paid while still being able to help people, come over here with us. But I wouldn't move. He was trying to recruit me for two years and I wouldn't move because it was less money in that work. And I always say it's less money in that work.
When I finally decided to move for the purpose and not for the money, everything just opened up because when I was about to transfer from one department, I'm a city employee. And when I was about to transfer from one department to over to the reentry center where I'd be able to help people, the assistant, the deputy city manager, she saw, she said, hey Oz, I got your paperwork. You going over to the reentry center? I say, yes, ma'am.
She said, I noticed that the pay is lower. I'm gonna make sure that you take your same pay over there with you. And it worked out. It worked out just like that. So I didn't even lose money. Yeah, I was worried. But I had made up in my mind to take less money for go for peace of mind and to be able to help people. And it worked out. know, the high power that it looks out when you move for the right reasons, it will work out.
Marcus Hart (21:50.991)
It becomes a violent appointment at that point, man. certainly it definitely works out that when you pretty much build to do something, you build to do this. And that brings me to my final question. It's knowing what you know now, do you think it's very important to have people who has experienced what you have experienced in these types of positions to ensure that we can move the needle?
more than what it has been moved over the years.
Oswald Newbold (22:23.156)
yeah, most definitely. how they say, I always mess it up. We say, what, nothing for us without us or something. They got a saying, something like that out there. And I believe that's true, but I think we still have to choose why, just cause you're, you're, you're, you're justice impacted. Don't mean you ready to lead just cause you did time. Don't mean you ready to help others. If you can't bear, if you can barely help yourself, how are you going to help others right then? So I think.
What we have to do is people impacted by the system do need to become, they do need to come to the forefront. We do need to be in leadership or we do need to at least be in like decision. We need to be in decision-making capacities or have some type of influence there. And we have to use it wisely because we can make, we can make 50 steps forward and all it takes is one wrong move for us. It's going to sit us back 200 steps.
because it's already up, we have to fight to get, as a matter of let me take them 50 steps away. It's hard to get two or three steps up. So if just one mess up, they're gonna still put us back two or 300 steps. And we got to fight our way back to them. But yes, it's imperative that we be in leadership, we be in now, but we have to be built for those moments because a lot of times we get in a fight, we thinking by self,
Marcus Hart (23:22.488)
It is free.
Marcus Hart (23:31.907)
Mm-hmm.
Oswald Newbold (23:51.366)
we got to think about the whole, it's me, it's you, it's our brothers and sister that's behind the wall, it's the ones awaiting a trial, it's the ones who really, that's in that class, that's about to take that standardized test that the teacher already got in their mind, like, man, he ain't gonna amount to nothing one day, he'll take the test. So it's bigger than, yeah, I seen how you had initially closed your eyes on that, but yeah, it happens in there, it happens.
Marcus Hart (24:21.205)
Yeah, yeah, yeah, I you know, I witnessed it, you know, I know, you know, know relatives, I know friends, you know, who've been in that spot and, you know, and it didn't go right for them, you know, because they didn't have nobody to like grab them and say, hey, this is the right direction. So, but on that note though, you know, where, you know, where can we get the book, Breaking Chains, Building Futures, and how can we get in touch with you if we want to get in touch with you?
Oswald Newbold (24:49.082)
Well, you can find the book, Chains, Breaking Chains Building Futures. They have it on Amazon. They have it on Barnes and Nobles. You could go on there to find the book. That's Breaking Chains Building Futures. It's on Barnes and Nobles and it's on Amazon. To get in touch with me, you can find me by name, Oswald Newbo at LinkedIn, Facebook, Instagram by name. Also www.oswaldnewbo.com. All those ways you could.
Get a hold of me.
Marcus Hart (25:21.55)
I appreciate you so much. This has definitely been an excellent conversation. We got so much more we could have unpacked. So I feel bad about the shortened time. But you're more than welcome to make a, know, spin the block again and chop it up with us, you know, no matter what you're doing in life. And we're right here to support you all the way. 100.
Oswald Newbold (25:29.33)
I'll hurt the nose.
Oswald Newbold (25:34.203)
No, no.
Oswald Newbold (25:45.01)
All right, thank you. And thank you for what you're doing to bring voice to issues and just doing what you're doing, Marcus.
Marcus Hart (25:53.528)
Thank you, thank you most definitely. those out there listening, the book of once again is Breaking Chains, Building Futures. Oswald, he contributed to that book and he has so much wealth to offer. So if you happen to pick up the book and then you read it and you get some forward, make sure you reach out to us and we make sure we reach out to him if you struggle to find out how to reach out to him. So once again, thank you guys for rocking with us.
Many blessings, peace and lots of love. out.