98: Defying the Odds — Jason Wang's Pivot from Prison to Helping Others Transform Their Hustle
8 Dec 2025 · 57 min
Transcript of a Pivot Podcast episode (host Jenny Blake) featuring Jason Wang, a formerly incarcerated entrepreneur and leader at Defy Ventures. Jason recounts his traumatic childhood, gang involvement, a 12-year sentence served partly in juvenile facilities, his transformation through education, mentorship and Defy Ventures, and his post-release entrepreneurship and advocacy. The conversation covers prison conditions, rehabilitation, recidivism statistics, Defy’s programs (entrepreneurship training, mentoring, pitch competitions), and calls to action for volunteers and supporters.
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Hello everybody. Welcome back to the Pivot Podcast. I am ecstatic to have Jason Wang here with us today. I met Jason at a mentoring night for Defy Ventures, which is an organization that provides entrepreneurship, employment and character development training for people with criminal histories and helps them build community and connect with mentors in the corporate and business and entrepreneurship world. I found out about Defy after reading Kathryn Hoak's book A Second Chance, which I heard her on an interview with Tim Ferriss. So you can see that I followed this amazing rabbit hole that led me to Jason, who was helping to organize the first mentoring night that I attended. And Jason was just bouncing around the room with the most incredible energy, the biggest smile. He had just proposed to his now fiance and I was so surprised at the end of the night to learn that he too had come up through a really tough childhood.
He's going to share his story with us here today on the show a little bit before we dive in. Jason himself knows a thing or two about being an underdog. Growing up as an only child of two immigrant parents living through poverty and abuse, he knows all too well the challenges of overcoming obstacles to transform generational legacies of poverty, crime and violence. Having received a second chance of his own, Jason is passionate about creating second chances for others through his work with Defy Ventures. Jason, welcome to the show.
Thank you, Jenny. Thank you for having me first.
You all don't know this yet, but Jason has the best laugh. We were troubleshooting before we hit record.
Jason, one thing that kind of blows me away is that you grew up with such tough circumstances and now you have this radiance and joy. I would love if you could just share with listeners a brief Your own history, growing up and. And then we'll get into some of the tools and resources that have helped you rebuild and reshape your life, which is so inspiring.
Sure. Well, I think that my life summary can be summed down to overcoming obstacles. Defy Ventures is really my second chance to give second chances. And in many cases, those second chances are really legitimate first chances in life.
When I was growing up, I grew up with two immigrant parents. My father was from China, my mom was from Malaysia. And they came to America seeking a land of prosperity, of being able to really build a new life for themselves. But when they came here, they had absolutely no friends, no family, no money in their pockets. We grew up in poverty. I was born in New Jersey. And on the block that I was born on, it was just rife with crime. We were just in poverty for as long as I can remember. My parents were working in a Chinese restaurant, working 14 hour days.
Six to seven days a week. And they were really seeking a better life for themselves, but they just didn't know what to do.
So my father had a really bad temper. And as I was growing up, the earliest memory of him, unfortunately, is of him abusing me. I remember him always telling me as a child that I would never amount to anything, that I wasn't his son, that I was a good for nothing. And he would take out his anger and frustration on me. I remember one time, it got so bad that he actually took a butcher knife and was chasing me around the kitchen trying to kill me. And so I grew up really.
Really feeling alone and not really understanding what love meant. I hated my family. And it got so bad to the point that by the age of 10, I had already attempted suicide three times.
At the age of 11, my parents got divorced and my mom decided to take me to go to Texas with her. And at that time, my mom had no college experience, she had no degree, she had no real job experience, and she had no idea on how to raise a son all by herself. And at that time, I was so angry at the world that I never even gave her a chance to become a mother.
At the age of 13, I ended up joining a gang. And the gang, to me, represented the family that I never had at home. I actually looked to the gang leader as a father figure. And in some families, the father plays catch with his kids or teaches them all of his hobbies or takes them out to sports. My father figure was teaching me how to commit crime. And so by the age of 15, I ended up committing a first degree felony aggregate robbery. And I was given a 12 year sentence, three of which I spent inside a juvenile facility where they housed kids between the ages of 10 and 20 years old.
I just, it's your childhood. I can't imagine the helplessness that you would feel under those circumstances and just, you don't know anything different. I was, I know I have been reading a lot of Gabor Mate's work and he writes about addiction and he says, find me one person who's significantly addicted to drugs or in the prison system who hasn't experienced significant childhood trauma. And that really opened my eyes up because up until reading Kat's book and encountering Defy, I hadn't done much inquiring into how do people end up in prison and how broken our criminal justice system is. But to understand that if you grew up with that kind of environment where your own father is trying to kill you, and as I heard you on another podcast, even having you work in the restaurants till you were, till 10pm when you're five years old, you know, like things that a lot of kids don't have to deal with. That of course, when you first find a gang in your teenage years and you have all those teenage hormones just like the our brain isn't even fully formed, of course that would feel like the most sensitive family you had probably ever known.
And I'm a firm believer that we aren't born out of the womb looking to become bad people. And in my experience, many people that have gone to prison are victims themselves. And that's not to say that we condone any criminal behavior. I hate crime. I hate criminals. And at Defy, we work with people with criminal histories, not criminals. But one example that I distinctly remember is one of my bunk mates when I was incarcerated and he was 13 years old there on a four year sentence. And he told me a little bit about his story and how life was for him growing up. And he told me about how his father was never in his life, that his father was always in prison or constantly going back to prison, that his mom was constantly strung out on drugs, that his sister was a prostitute, that they lived in a neighborhood where there would be drive bys or it was filled with gangs. And one of the reasons why he ended up in prison is because a rival gang member came up to him and threatened the life of him and his four year old little sister. And he retaliated and defended himself and he, he made a really bad decision, but that was one of the reasons why he ended up in prison. And I think that when we develop empathy and see through the eyes of other people and what their stories are and how they grow up, it gives us a better understanding of the context for which why some, or maybe even the majority of people, in my experience, the majority of people end up in prison and why it's so important to provide them programming so that way they can lead productive lives and leave this generational legacy of crime, poverty, and violence.
We also.
Sentence. So in the case of the bunkmate that you just described, I think this gets so complicated because as you said, none of us would ever endorse crime or violence. But if we put ourselves in his shoes, you can see how helpless he felt in that context of his life and kind of in defending himself and his sister. And then we end up sentencing children basically to 10, 20 years. And so in your case, your sentence was 12 years. What went through your mind at that time? I can't even fathom staring down what would, what you thought at the time would be a 12 year sentence.
Yeah. So when I went to court, I remember the first place that they sent me to was a detention center. And that's a place where you're basically being held awaiting your court date. And growing up, I was extremely Christian. My grandma would force me to go to church every single weekend. I grew up with my grandma, you know, reading the Bible out to me. I had like 16 Bibles at home that I would read. But I had really forgotten religion once I started getting into my teen years. Well, lo and behold, I get locked up and I become super religious and I start leading Bible studies. And leading up to my court date, I actually start fasting and all this other stuff. Right. Believing that, you know, if I did all of these, if I went into humility, like God would save me and not send me to prison. I did it for a very selfish reason.
So I get up to my court date and they're about to give me my sentence, and I hear my mom and my grandma crying behind me. And it's like I have no feeling left in my body. I'm just. I'm just sitting there awaiting my fate. And the judge says, jason, because of the seriousness of your offense, I'm giving you a 12 year sentence. And right after that happened, I just tuned out. I had a ringing in my ears. And.
As a 15 year old, 12 years seemed like the rest of my life. And so everything after that was a blur. But I remember when I got back to my bunk later on that night, I just started crying. My eyes out because I felt like I had no future and that I would be in prison for the rest of my life.
It's so intense. And you described it, so isn't there a name for it? They call it prison God. Like finding religion. Tell me what that even means.
Yeah. So prison God is when you go to prison and all of a sudden you find your faith and you're all about Jesus and you're all about the Bible, and nothing can tell you otherwise. And it's kind of like your lifeboat in this sea of helplessness and hopelessness that you kind of cling onto, because it's the only thing that you have. It's the only hope you have to keep moving forward. And so there are many people in prison that end up going that route, and in some cases, it's very beneficial. They actually end up transforming their lives through this, and I think it's great.
Yeah, it seems like a really crucial tool, actually, that in a system that can be so dehumanizing, that, especially again in the States, is so broken, that. That this is a resource and that. It seems like I would get the sense that it's one of the primary ways that people do pull themselves through the prison experience and come out on the other side with. With a new take on life.
Yeah. I mean, think about a living space the size of a parking lot, and that is where you live for the rest of your sentence. I was incarcerated with kids, you know, as young as 11 years old. They would go in there for crimes like graffiti, maybe truancy, maybe they stole something from a store. And because there was very little programming in the facility that I was locked up at.
Many of them just ended up becoming better criminals. They learned from other people how to become better criminals. And for the average person who spent time inside a juvenile facility in Texas at the time, which is where I was incarcerated, it was four and a half years. So imagine going to prison at the age of 11 and coming out when you're 16. The years where you really start to develop who you are as a person and what your identity is, and really not having any pathway or even knowledge of what the other side of the road looks like. Like, you know, like getting a legal job or, you know, being a good role model for your kids, families, communities. You're. You learn that prison is the rest of your life, and that's just what you grow up into.
What do you think makes the difference between men and women in prison who are somehow able to find hope and transformation and the desire to change? Knowing how incredibly difficult we make it for formerly incarcerated men and women after they get out. Like, they can't vote, they can't get jobs, they can't get housing. It's extremely challenging. How, what, what makes the difference between those who have this awakening in prison like you, and kind of coming on the other side with a new lease on life compared to those who might just feel that the crimes they did are sort of justified in the way of life, and this is all they have. And they're hopeless. And I would understand that hopelessness as well, given the context of how they've grown up and how they're now spending 10, 20 years behind bars.
Yeah, so unfortunately, the vast majority of people that go to prison don't end up finding that hope. Statistically, 76.6% of people that go to prison will end up back in prison within five years, and 95% of people that go to prison will end up back in the community at some point. So in prison systems that don't offer rehabilitation or any type of programs, at the end of the day, what type of neighbor do you want to live next to? Because these guys are getting out, these men and women are getting out, and we don't give them something to cling on to, some hope that they can create a future for themselves, they're going to end up back in prison. 89% of people that get re arrested are unemployed. And the cost of incarceration is staggering. So here in New York city, it costs $60,000 to incarcerate one person for one year. In New York City, for example, it costs $167,000 to incarcerate one person FOR ONE YEAR. And it's not working. We're not making our community safer. It's not a good thing to spend all of this money when that could be diverted to, let's say, the MTA or the subway, for example, or let's say even to educators. I was very fortunate when I first went to prison because I had my mother. And even though I hated her before I went to prison, it's only until I went to prison that I started to realize how much she loved me and what a mother's love actually meant. When I was first incarcerated, I was arrested in the garage of my home. I pulled my car into the garage. I had gotten out of the car, two squad cars pulled up behind me, guns drawn, and they arrested me right there on the spot. And at the time, my mom was working 12 hour night shifts, you know, lifting boxes and moving things. She's Like a five foot two little Asian woman. And she was breaking her back in order to provide us a life. And because we were making so much commotion in the garage, she came out and she saw me getting arrested for the first time. And I had hid so much of what I was doing away from her, but inside, she knew that I was hanging with a bad crowd and that I was getting into trouble. But despite all of that, when the cops were arresting me, she looked at them, she said, you must have gotten the wrong person, because my son would never do anything to harm somebody else. And I still remember that to this day. The second thing was that when I went to court, my mom gave up her entire life savings, $10,000, to pay for her attorney, without even thinking about it, in order to help me get out of prison. And then when I finally did go to prison, they sent me to a prison in South Texas, which is about seven and a half hours away from Dallas. And my mom and my grandma, they bought a minivan, and they would drive those seven and a half hours down to prison to see me every single weekend for two hours. And then they would drive all the way back home. One of the reasons why my mom bought the minivan is because on nights that she just was too tired, she would drive as far as she could, pull over to the side of the road, sleep in the van, and then keep going. I think the last piece was when I went to prison, I used to get these huge packets of mail. And I used to think that, you know, some of the girls that I used to talk to or some of my old homeboys or, you know, guys from the gang. My mom was actually sending me math homework.
Go, mom.
When she came to visit me, she would test me on the matt homework. She would send me articles on, like, religion, on geology, on investing, on business. She said that although I was physically in prison, mentally and emotionally, she was in prison. And the only way that she knew how to keep me safe was to provide me material to keep me busy. And so it's because of my mom that I am the man that I am today, that I started to believe in myself, that I didn't have to spend the rest of my life in prison. And unfortunately for many folks that are incarcerated, they don't have that type of family support, especially if you've been locked up for many, many years. The visits just start really coming in less and less.
It's so incredible that your mom showed up for you in that way and your grandma, and that it shows the power of Having even one person in your life who says, I still got you, I'm going to bring you math homework. You mentioned articles on religion. Just keeping you busy. And then what I love and I find so interesting about you is that you then started teaching GED classes in prison. How did you. What was it that spark within you that said, all right, I'm getting this help. Not everyone has it. I'm going to give back even while I'm here.
So. So education is a weird thing.
Laugh. I love.
You know, so when I was in prison, I ended up not joining a gang. I went solo, which means that. So when. So oftentimes when people go to prison, it's very racially segregated. And so if you're white, you end up going to gangs like the Aryan Brotherhood. If you're Hispanic, you go gangs like the Mexican Mafia or MS.13. If you're black, then you end up going with the Bloods, the Crips, Black Guerrilla Family, whatever it is. And gangs are really a source of protection.
From other rival gangs. But unfortunately, it also leads you down this path of crime as well, because in order to stay in a gang, you have to put in work. Well, I was a unique case because I'm Chinese, and when I went to prison, I was actually the first Chinese person that they've had in their facility in the past 10.
Really?
Wow.
There's a badge. That's crazy.
Yeah, it's something I put on my resume.
Yeah.
And so, you know, one of my nicknames was Bruce Lee and Chino whenever I was locked out.
Oh, my gosh. I would think that going solo would be dangerous somehow, that because you didn't have a group behind you, would you be susceptible to all these other groups kind of ganging up on you?
Well, yeah. I mean, I had to. I had to, you know, throw fists a couple times and show off a couple of spinning sidekicks. You know.
We had you taken martial arts growing up.
Yeah, actually, when I was growing up, I used to take Taekwondo, Tang Soo Dorade. I used to be in all that stuff. Unfortunately, it doesn't really translate into an actual street fight, so.
But you were able to fend for yourself enough to say, I'm not gonna be your punching bag.
Yeah. I mean, I went in there with basically the mindset of, I don't care what happens to me. I don't care if I get beat. But I am going to give whoever's gonna give me trouble. I mean, give them hell. And I'm gonna make sure that if they think about messing with me that they're gonna leave with a couple of scars. So that was my initial mindset. When I first went to prison. I was scared more than anything else, and I just. I just had no idea what to do.
But funnily enough, education really actually turned to be.
A turning point for me and for other people that were incarcerated as well. So in prison, we had kids ranging between 10 and 20 years old. We had 18 years old that, like, didn't even know how to read. You know, we had 14 year olds that didn't know basic math. And because there was such a wide range of education levels, whenever we would go to classrooms, instead of teaching us, they actually gave us crossword puzzles to keep us busy. And that was. That's basically your education for the three, four, five years that you're incarcerated. So because my mom was sending me all these books, I was fairly well educated. And so in my free time, I decided, well, why not start up a GED class where I would teach other people how to get their GEDs? And I was skeptical at first because I thought that nobody would actually care to do this. But I ended up recruiting a couple of folks. We would go into a group room, I asked for some pencils, some paper, and a GED book, and I started teaching people how to do basic math or how to read and help them get their GEDs. And what I started to realize was that once people started to get it, once they start to learn one thing and start to master it, they were so hungry to learn more. Because for the first time in their lives, they are, you know, they are proving that they can be more than just an ex gang member or a criminal. They're actually doing something and they're learning something. And so it became a program that we started instituting throughout the entire prison.
That is incredible. It must have been so powerful to empower these. I'm guessing it was mostly men. I mean, yes, you must have been in an all male prison.
Can't see the thing makes them okay.
But to empower these men and to be a teacher in their lives when maybe they really hadn't had much of that.
Yeah, I mean, for. For many people that are incarcerated, they have people that walk out of. Out of their lives all the time when they're growing up, Whether it's their fathers or they're being told as a kid that you'll never amount to anything. Just like I was when I was a kid.
Many of them grow up believing that going to prison is a badge of honor and that they Want to carry on the family business of drug dealing or gang leading. And that's just what they're taught. When I was growing up, I never thought that I would live past the age of 21. And so if you don't see a life past 21, why does education matter? You know, why does going to college matter? Why does getting a job matter if you're not going to live much longer anyways?
So when you were in prison and your mom, because your dad had told you you're not going to amount to anything, but here was your mom sending you math homework and quizzing you and showing up and what made the shift, did something shift for you while you were in prison where you came to believe, okay, maybe I will live past 21, or even I want to live past 21. And because also, and I'm curious to hear where defy enters the picture as well, or at least, Catherine, maybe it was pre defy. But getting out of prison isn't easy either. I mean, there's so many challenges that people face upon getting out, even with the best of intentions and the highest hopes. So how did you hang on to that spark that was starting to form in you?
Yeah, so, I mean, part of it was every single time that my mom came to see me in visitation.
The first, like 15 minutes was always just a soft fist. Like she'd be crying her eyes out, but she would always end the visit by telling me that she loved me and to not forget who I was, to not give in to the negativity around me and that I would do better in life. She believed in me and she gave me hope that I could do better for myself. I think the other thing was that during that time in 2006, there was a huge scandal going across organization. And basically they found that correctional officers were taking.
Boys and girls, putting them into isolation cells and sexually assaulting them. It was one of the worst times, if there even is a good time, to be in prison. There was this widespread corruption. There were human rights abuses. One of my bunk mates, he was involved in a riot where a correctional officer ended up picking him up and throwing him so hard into the ground that he went blind in one eye and leaving him in an ant pile in 115° South Texas heat for hours. And he ended up having bites all over his body like he was severely burnt. Like, that was the type of environment that I was in now through this adversity and this kind of helpless environment. Because of my mom's encouragement, I kept a positive attitude. I Did well in school. I passed my ged. I started doing these Bible study and GED classes. And so I became a trustee at the facility. I was working all types of jobs, making 25 cents an hour, which I thought made me the richest guy in the world. But one of the things that it allowed me to do was the federal government looked at that facility and said, we're thinking about shutting it down. And so at the age of 16, the facility actually brought me over to McAllen to testify in front of the Texas Senate and to advocate on the behalf of inmates and to talk about our experience. And it was after that that I started to realize, you know what? I think I have a voice. I think that I can actually make a difference. And that if I continue to be positive, if I continue to try to change the lives of other people around me, then maybe I don't have to be in prison for the rest of my life. Maybe I'll have a future past this. And so it was a culmination of my mom really believing in me and saying that you can do it and to not give in to the pressures around you and just being stuck in a really, really tough environment and overcoming that obstacle, that really kind of shaped my life moving forward.
And when did you meet Kat and get involved with Defy?
Yeah. So Kathryn Hoke, she is the founder of Defy Ventures. She is also the founder of the prison entrepreneurship program, which is kind of a precursor for Defy. And I met Kat about a week before I was getting released, and she came to the prison and she basically said, hey, I've got a program where I can teach you how to transform your hustle to legal enterprises. Her thesis was that many people that sell drugs or lead gangs are running for profit organizations that have better profit margins than some technology companies. If you look at a gang organization, they have a board of directors, they have bylaws, they have sales strategies, marketing strategies, logistics, wholesaling. This is a for profit business. And what she realized in one of her prison visits was that these men and women are natural born hustlers that really just don't know how to direct their innate business skills towards something positive. So she talked to me about joining this program. I was really skeptical at first because I was thinking, like, you're crazy. Like, you think that I'm actually going to be an entrepreneur? Like, you've got to be kidding me.
And by the way, what perfect timing that she came a week before you were getting released.
I know, I know.
And just so we were in context Was this right after you testified? Were you still around 16 or 17 years old?
I was 18 years old at the time, so it was about a year and a half I testified.
Okay.
And so she talked to me about this organization. I chose to accept her challenge. She's very competitive, and she likes to challenge people. And she was. She was like, are you brave enough to join this organization, to change your life?
And I said, yes. So I joined the prison entrepreneurship program, and.
They equipped me with a mentor. They had an incubator program where they partnered with Baylor University and the University of Dallas. They had volunteer executives, entrepreneurs, and investors that taught us how to create for profit businesses. And six months after I was released, I started my first business, Wang Innovations, and I started creating computers, 3D computer simulation projects for civil law cases. And in my first case, I won my client over half.
What's your business idea, by the way?
Yeah, I mean, I. When I first was released, they equipped me with a mentor, and basically they said, hey, Jason, you know, he's got felony eyes record. He's probably not going to be able to get a job. Can you help him? And so my mentor ended up introducing me to one of his other very rich friends who happened to be attorney, and they had a civil law case that they were suing an insurance company. But, you know, to make a long story short, they wanted me to take pictures of the damages of the building and put it onto a PowerPoint slide. And then that's when the light bulb came out in my own head, and I thought back to that movie Titanic. Have you ever seen that?
Yeah. Yeah.
So you know that. That first part where you see a 3D computer simulation of the ship sinking?
Yeah.
So I thought, well, why don't we do something like that for this project? And so they got super excited and they said, yeah, let's go ahead and do it. And I started sweating because I had no idea how to do this. And so I reached out to every architect and engineer that I could get a hold of, and they taught me this program, and I lived and breathed that program. And in the end, I was able to build this 3D blueprint of the entire building. And. And it was a program where you could actually walk through the building. You could take it, you could rotate it, you can go floor by floor, and as you walked into each room, you could zoom in and see pictures of damages to that particular room or to that particular floor. And that's what we presented during the civil lawsuit.
Oh, my goodness. That is so incredible. And how much did you say you helped them win?
So we ended up winning them over a half a million dollars.
Oh, my goodness. That's so what I love. It's so Pivot friendly. What I talk about is kind of finding something that you already know or the intersection of your past experiences and your strengths. And so it's amazing that although you didn't know 3D design, I don't know what software were you using.
So I started using a program called Google Sketchup, and it was free.
Yeah. I was wondering if it was SketchUp.
As an entrepreneur, they taught me how to create a lean business with very low overhead. And so that was the.
But applying it to criminal justice and actually applying it to an area that you knew and were passionate about and had experience with, and that. That you were scrappy enough to teach yourself SketchUp and add that in. And so. Wow, amazing. And so you were in this program and then by the time I met you, which is. How old are you now?
I'm 28.
28, wow. So we're almost 10. We're about 10 years later.
Well, you look like you're 21, though.
You. You do. Yeah. But wait, so now you're actually.
In charge of executive relations for Defy. So I think that Pivot's also very interesting of how you went from kind of working on your own business ideas as a participant in the program to actually working in executive relations. Can you tell us how you made that switch?
Yeah. So Kat was running the program in Texas, the prison entrepreneurship program, and then she left that organization and started Defy Ventures. Defy Ventures is entrepreneurship and employment training platform for people with criminal histories. What we do is we use our love for entrepreneurship to host Shark Tank style business pitch competitions and incubator program and pair it with a whole lot of character and leadership development to help men, women, and youth, some of America's biggest underdogs, to win every single day. I got involved with the program after reaching out to Kat after I've been released for a number of years, and she said, hey, you should join this program that I started. They had already been about four or five years in the making. They were generating amazing results. And she said that you should join this program and start another business. And so every time I meet Kat, I end up starting another business. And that's exactly what happened. So I joined the program in 2015, and I created a technology company called Bite Size Moments. It was a video platform for e commerce companies. And over the course of two years, I ended up hiring four to five Other people that started working for my company, we were scaling all across the nation. And then I ran into a challenge. And the challenge was that I had quit my job in management consulting. I had sold everything that I had. I had gone 100% all in into this company to continue to finance it. I had gotten deep into credit card debt, and I was at the very end of being able to keep the company moving forward. And so I started going out to angel investors in Texas. We were looking for $1.5 million for our seed round, and I was asking him for money. And what I started to realize is that after talking to about 30, 40, 50 investors that unfortunately, due to my criminal history, many of them were not open to the idea of second chances or to a person that wanted to create a business that just happened to have a criminal background. And every single time during my pitch or if they would find out after that I had a criminal history, they would kick me out of the door.
So I ended up failing, and I had to shut down my business, which was the second hardest thing after prison that I've ever done. And then at that point, I really had a decision.
Do I go back into management consulting and work a job? Or at my lowest point, do I decide to take another risk and do something that I'm truly passionate about? And I had seen the effect that Defy has had in my own life and in life of my family, and I decided that, you know, I would jump ship over to New York and work. And I've been working at Defy ever since.
Wow. It's so amazing. One of the things you described is how. And it's called different things. I'm also reading Michelle Alexander's the New Jim Crow. About. She describes it as this invisible cage because someone might be out of prison, but we have restrictions on education, employment, housing, and voting. And each of those is one bar. So alone, it's not a prison. But by the time that each of those invisible bars is put up, it kind of really holds people back. And as you described it and Kat says it so well, it's like, you know, what's the worst thing you've ever done in your life? And how would you like to be known for that the rest of your life to be carrying around?
Just, you know, we've all done things we're not proud of, but we don't have to be labeled by it constantly and be constantly reminded. So I just. I think it's so powerful what you're doing. And with Defy, and I have to Say I didn't know what to expect from the first mentoring night. I just felt really called to go after reading her book and just after reading other, other books as well. Just Mercy is a book about a lawyer who works with men on death row. And I just developed so much more nuance and I didn't know what to expect. And I don't want to stereotype EITs, which is entrepreneurs in training, but like, man, are they some of the warmest, most loving, like brightest people. I couldn't believe it. I just, I didn't expect that for men and women who had been in prison for some of them 20 years. They're like to be so loving on the other side. Like they would have every reason not to be that way, but I just couldn't believe it. We just had one last night, the day before recording this. And I leave with such warmth, you know, like, I get probably more out of it than even the its who are there attending or hopefully we all get the same.
But yeah, well, so in a lot of my speaking engagement. So that is a viewpoint that many of our volunteers share. We have over 4400 volunteers all across the nation. We're a national program. And I do a lot of speaking engagements for DEFY here in New York. And to your point, one of the things that I ask is, what would you do if you were only known for the worst thing that you've ever done? And I pause and I let people think about that and the labels that would accompany that. Would it be ex liar, ex thief, ex drunk, whatever it is. And I, I believe that we are all X somethings. But for the people that I advocate for, they're known as ex offender for the rest of our lives. And.
The people that I advocate for, they have made grave mistakes in their past. One of the things that DEFY teaches is to take ownership of your past bad choices and of your past mistakes. So we own what we've done in.
The past, you mean rather than saying, well, I did what had to be done, or as Kat points out, there's the language. I caught a case like as if it's a flu or something.
Yeah, because if you don't take ownership of the things that you've done in the past, then you're more likely to end up continuing to do it because it's not your fault. And so that's one of the biggest pieces of DEFY is to take ownership of the past, take ownership of your actions, and to also, you know, to. It's part of the cycle of learning how to break these negative thoughts and to break the cycle of incarceration. And so the people that I advocate for, yes, they've made horrible decisions, but then the criminal justice system.
Sentences them and sends them to prison and they supposedly pay their debt to society and.
By the way, disproportionately sends them to prison. Like according to income and ethnicity. It's really completely broken and unfair of who goes to prison and for how long. I mean, even reading about the difference between the person caught with the same amount of crack would need 100 times the amount of cocaine to get the same prison sentence of 10 years.
Yeah, like, African Americans in this country are about 30% of the population, but they consist of 60% of the prison population. And then we look at certain cases like, do you ever. Have you heard of that case of Brock Turner, the, the Stanford swimmer boy? Yeah, yeah, so. So he was a blond hair, blue eyed, white male going to Stanford, and apparently he swam really, really fast, but he raped a girl behind a dumpster and ended up, I think, getting like six months of like, community service. Or maybe he maybe committed some, you know, did some time. I don't, I don't even remember. But imagine if you were a minority or if you came from a low socioeconomic background, like, you'd be in prison for the rest of your life. And that is part of why I'm so passionate about the work that we do, because this is not justice. This is not. This is targeting people that happen to look differently than, you know, white rich people that can maybe buy themselves out of almost anything and their lives are ruined because of it. One of the things that is most heartbreaking to me is that 70% of kids that have a parent who's incarcerated will end up following in their footsteps. And that is one hell of a legacy to inherit.
One thing that Kat talked about, which I'm curious to hear your take, she said, you know, she encourages or teaches people how to tell their story in a way that does not evoke pity. What does that mean? And what's the difference? And then part two of that question is, I'm curious, for those of us, let's say, who haven't been incarcerated.
Just what you'd want us to, like, open our eyes to or how we can.
Communicate around this without. Without similarly evoking pity, let's say, or, you know, giving some response that isn't actually helpful. I don't know if that makes sense.
So at defy, like, pity does not help anybody. Pity is.
And let's give me an example of, like, a story that evokes pity of this. This happened to me, and you should, like, feel sorry for me kind of.
Yeah, sure. So we have an EIT and entrepreneur in training. That's. That's what we call the people that we serve. We call them.
I love that we have now a positive label like that isn't just, yeah, ex convict or formerly incarcerated. It's like, oh, they're EITs.
It's. Yeah, yeah. So at DEFY, we use the term EIT. At the prison entrepreneurship program, we used to use suite names. And so I'm swearing you and your audience to secrecy.
Okay.
I told many people this, but my sweet name when I was in the prison entrepreneurship program was Little Princess.
Little Princess.
Little Princess. And the whole point of these sweet names is to break away from, like, you know, the old gang names like 3, 5, Killa, or whatever deal is. Like, by breaking down these stereotypes and these barriers, you're able to really transform your lives. Because if we're always known as, like, a gang name, then we're always going to identify as a gang member. So at defy, we like to level the playing field. But to your, to your question, we. We have one of our EITs in California. His name is Justin, and he was the product of a conjugal visit with his father and mother. So he was born with his father in prison. When he was growing up, all he knew was that he was never going to go anywhere in life and that he was destined to go back to prison. And today he's back in prison himself.
And he's ended up joining our program. He's doing amazing things. But that's a story that many of our EIT share. Like, they have these heartbreaking stories of, you know, at the age of five, they saw their first murder, or at the age of seven, they were given drugs and told to sell cocaine or crack or whatever it is. And for people that have never experienced that side of life, it may be very easy to go in there and pity these folks. But we, we are totally against that. So whenever a volunteer comes into prison with us, we like to level the playing field. And so we make our volunteers do the same thing that our entrepreneurs do. So for many of our entrepreneurs, they are training from anywhere between six to 12 months to get ready for a Shark Tank competition where they will be pitching their businesses for real money in front of executive judges like Sheryl Sandberg, like Tim Draper, like Mark Zuster, like Brad Feld, and they are essentially trying to launch businesses upon release. And so one of the ways that we level the playing field is that when volunteers come in, we ask them to introduce themselves and dance up to the front of the room to allow themselves to become vulnerable, because that's the same thing that we expect from our EITs. And when you look at some of our EITs, like, these are old, like, gang members that are super, super tough. But they say that pitching in front of these judges is the scariest thing that they've ever done in their lives. And so we love to break down the barriers to level the playing field. We do an exercise called Step to the Line, where it's two strips of tape down the middle of a prison floor, and we have all the volunteers on one side and all the EITs on the other side. And we'll call out questions, and we'll start off really easy. So we'll be like, you know, how many of you were the class clown whenever you're growing up? And if that's true for you, then you step to the line. But then we dig in a lot deeper. So how many of you dropped out of high school? And many times, many of our EITs will step to the line, and none of our volunteers will. We'll ask questions like, how many of you have a college degree? All the volunteers stepped in line. Almost none of our EITs, and we keep going down that path. How many of you have committed a violent crime? And almost all of our EIT step to the line. But in many cases, almost none of our volunteers step to the line. And then we kind of dig into that a little bit deeper. So for many people, you know, getting into a schoolyard fight, you know, fighting off a bully, maybe you were fighting with your sibling.
For many of our volunteers, they don't consider that a violent crime. But for many of our EITs, that's what they end up getting arrested for, sometimes by as early as the age of seven. And so when we start to really dig into it and talk about how, you know, have you ever done anything that you could have been arrested for, but you didn't, slowly our volunteers start stepping to the line. When we talk about, you know, have you ever held weed? Or have you ever had a couple of beers and gotten behind the wheel of a car? Or, you know, in some states, if you steal somebody else's WI Fi, that's considered a felony. And people start to realize that, yes, many of them have done things in their life that they could have been arrested for, but for maybe because of the color of their skin or their economic backgrounds, they don't. And it's a really powerful exercise that really brings people together, not in their differences, but how similar they are as human beings.
That's so powerful.
Yeah, I just, I think that it makes a lot of sense. And you know, there's a lot of talk just in society now about not just unconscious bias, but like unconscious privilege of people. You know, there's of course the term white privilege, but there's also just class privilege, social privilege, like advantages that people don't even realize that they have had. I'm reading hillbilly Elegy by J.D. vance, which was this mega bestseller on the New York Times, and I'm only finally getting around to it. And he describes, even though he's Caucasian, he grew up with, you know, and then he ended up at Yale Law School, but by like many miracles of his own upbringing. But he's like, it was the class differences that were so challenging for him and just having that awareness that even a lot of entrepreneurs talk about bootstrapping. And I used to use the language of like bootstrapping my business, but we don't realize what enormous communities surround us that not everybody has. And what if you could have a call to action for Pivot podcast listeners or if there's something, maybe, maybe you can give us two things, something they could do in their everyday life. Like that might relate to our conversation today. And then of course, if people feel called to get involved with defy, what that might look like.
Sure. So when you look at defy's mission statement, it's to transform the lives of business leaders and people with criminal histories through the entrepreneurship journey. We don't just serve people with criminal histories, but we help people that are business leaders get through some of the, maybe some of the obstacles that they face in their own life. You don't have to be in prison to be in a prison. One of the things that we teach to our EITs is to get past self limiting beliefs. And these are beliefs like you're a bad father or you're a crook, or you're never going to be good enough. And these are things that we tell ourselves unconsciously that hold us back from being the best human being that we can be. And so for our volunteers or for anybody out there that's listening that may be going through this as well, I would say is you are not the worst decision you've ever made or you are not the worst thing you've ever done.
And I think that when we learn how to forgive ourselves is when we can really go on.
To really tap into our greatest potential.
So that's one thing that I would impart to anybody who's listening. It's something that I've dealt with in my own life. When I came out of prison, I was ashamed. And even to this day, I carry this shame that will live with me for the rest of my life because of the things that I've done in my past.
Just a couple days ago, you know, I woke up in the middle of the night because I had this dream that I was back in prison or I think back to some of the things I used to do and I just break down in tears because of the person that I used to be. But forgiveness is for everyone in that we can all forgive ourselves and we don't have to be in prison mentally or emotionally to things that we've done. The second thing is that if you're looking to get into a cause that produces tangible results, we have a less than 5% return to prison rate, which I think is the lowest that I've seen. It's one of the lowest I've seen for a program at scale. We serve more than 2,500 people across the nation, across five different states. California, Colorado, Nebraska, Connecticut, New York. If you're looking to apply your, you know, take your business hat and apply it toward, you know, human beings that are truly trying to transform their lives, then Defy Ventures is the organization for you. You can find us at www.DefyVentures.org. you can follow me on Twitter at Jason Wang. That's W A A n G. So it's Jason Wang.
I post, you know, our prison events and post release events all the time on there. Or you can email me at jwang J w a n geventures.org to inquire about upcoming prison visits or post release events or even shark tank competitions where you can come and be a judge or help somebody with a business idea or with a resume and coach them. So those, those are just a couple of different options.
Amazing. I love your advice to all of us in the ways that we sometimes imprison ourselves and the burdens that we carry or, you know, it doesn't, it doesn't take extreme stories or situations even to create kind of lifelong struggles that, that we see. And, and I just, you mentioned even earlier about sharing your story and one of the things that I've been so amazed by and just blown away by are people like you and Terrell who was leading last night and the stories. I think you come out with such an incredible story and that it just reminds me of the power of sharing those. And I hope that everyone listening found this as powerful as I did. And Jason, I could talk to you all day. I just want to thank you so much and I hope that all of you, I wish that you will get a chance to meet Jason in person because he just bounces around the room like a ball of light and it's the most bubbly, smiley, gregarious guy, probably one of the ones I've probably ever met. So it's just really beautiful to see.
Where you've taken things, Jason. And I'm grateful to know you and I'm just super thankful for you sharing your incredible insights with all of us on this show.
Yes, thank you for using your platform to help us transform Hustle. And I am very honored, honored and really excited that I was given this opportunity. So thank you for using your platform for good.
Thank you, Jason. And yeah, if any of you listening get a chance to attend a mentoring night, it is really incredible. I just can't say enough good things about it. And as soon as I left the first one, I just told the organizer, I said, sign me up for all of them. Like all of them. If I'm in town, I'm there. And I count down the days in between of when I can go back. So thank you again, Jason.
Thanks so much for listening to this episode of the Pivot podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com podcast and connect with me on Twitter ennyblake.
Remember, build first, then your courage will follow.
Hasn't it always Sam.
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