Episode 22: Jason Wang | From Convict to CEO
Updated: Oct 15, 2019
"You know, you don't have to physically be in prison to be in prison. Many of us put ourselves in mental and emotional prisons because we haven't chosen to forgive ourselves."
Below is an abridged audio transcript of Episode 22, the first episode for Season 3 of Rock The Boat: Against All Odds, edited for clarity.
Rock the Boat is all about Asian Americans who are challenging the status quo and breaking stereotypes. This week we feature Jason Wang, a former gang member and ex-convict who is now the founder of a company called FreeWorld that provides employment opportunities for people with criminal histories. He says the incarcerated are one of the least served labor pools in the country.
Jason got very personal with us, in part because so much of his upbringing and family history has shaped who he is today, and why he thinks it is so important to give people—especially ex-convicts—a second chance.
Trigger Warning: This interview includes references to domestic violence, abuse, and suicide. So if any of these topics make you uncomfortable, we recommend you skip this episode.
This conversation with Jason covers topics ranging from:
His personal story about his abusive father
Joining a gang as a teenager
Getting caught and going to juvenile detention
What it's like to go to prison
Teaching others in prison math and bible studies
Getting out of prison and starting a company
I. Jason's Origin Story
Jason: My name is Jason and I am the founder and CEO of Free world. Free world is an educational investor in America's biggest underdogs and most overlooked Talent pools and that's people with criminal histories.
My parents were immigrants. They came from China and Malaysia and they really came to America seeking the American dream.
So they were looking forward to the white picket fence and two car garage. They were looking for Second Chances an opportunity to move up economically that they normally wouldn't have in in Asia. //
My father was really going to pound in the idea of hard work while my mom was trying to pound in the idea of education. My parents were extremely poor and my father was really the head of the household.
My dad did take it to the extreme. And so when I was a young kid growing up, I grew up with a lot of abuse and there were times when my father would get so angry that he would take up a butcher knife and chase me around the kitchen trying to stab him.
By the age of 10, I had already attempted suicide three times and I just really felt alone and unsure of who I could go to for help.
Lucia: When Jason’s father came to the United States, he ended up getting involved with an Asian gang called Snakeheads.
Lynne: Snakeheads, by the way, are Chinese gangs that are mostly set up to smuggle people into wealthier, Western countries.
Lucia: Yup. Like places like the US.
Lynne: But according to Jason’s story, they are also set up to do other things—like maybe financially support your business. So Jason tells us that his Dad ended up borrowing millions of dollars from this gang in order to set up a trucking business. But the business didn’t succeed, and when it went up flames, his family received threats.
Jason: So when the game came asking for their money back, they went up to my father and essentially showed them a picture of me and my mother and my grandmother and said that we are going to kill your entire family unless you pay this back. And so what my father did was he ran and so we went from state to state working at small little Chinese restaurants and so he could save up the money
Lucia: They ended up in Carroll, Iowa, where the population of minorities was pretty small. At the age of six, Jason started bussing tables and cooking in the kitchen of this Chinese restaurant with his father.
At 11, Jason’s parents got divorced. It turned out his dad had three kids and a wife in China. So his mom and him left his Dad and moved to Texas.
Lynne: And life was very different for Jason. He wasn’t afraid of his dad anymore. He wasn’t afraid of his mom.
Lucia: Jason says he became extremely rebellious, adopting this “me-against-the-world” attitude.
Lynne: Yep, Jason believed he had to do whatever he needed to do to survive.
Lucia: At 13, Jason joined a gang.
Jason: I ended up meeting this group of people that happen to be in a small Asian treat game and I start hanging out with them and we go street racing into fights and drink and do drugs and I to me that felt like a family that accepted me finally, you know, we were committing crimes together and even though I knew it was wrong at the time.
I have this yearning for respect and a sense of belonging and that's what the gang provided for me when I didn't have at home. I think the other thing is that the gang leader really turned out to me as a father figure and he cared and respected me and nurtured me to move up in the gang and to commit larger murder crimes.
II. Jason gets caught and goes to jail
Lynne: At age 15, Jason was incarcerated for a group 3 felony—aggravated robbery—and was given a 12-year-sentence.
Lucia: Jason’s gang would scope out houses and plan these robberies sometimes a year in advance. They’d figure out where the nearest fire department and police station was. They were armed with walkie-talkies and halloween costumes—they’d even practice on other houses.
Lynne: These were pretty elaborate stunts.
Jason: It was a Saturday. We dress up as electricians. We went up to the front of the house and we knocked on the door and there's three of us and we told the woman in the front that there was a Transformer blew out in the neighborhood and that we need to check her fuse box and show she allowed us to come inside the house.
We went over to the garage and that's when the gang leader pulled out a gun and told her that if she made a sound that we would we would kill her. There we all had our responsibilities we knew exactly who was in the house. And so we went to each of the rooms and Tighter victims up and put them into a living room with a ghost.
And from there. We went and basically ransacked it looking for a safe that contains 75 thousand dollars worth of cash as well as two rings one costing 25,000 other one costing 35,000. Halfway through we received a communication from our Lookout saying that there was the car that had just broken from the host and that we should expect somebody come in.
And so we hid, the uncle ended up coming into the house.
We tackled him to the ground and basically threatened to kill the son if they didn't open up the safe.
Eventually, we got the safe and all the things that we were looking for. We piled it into the car and then we drove away to get away car where we transfer the goods and then we took those goods over to a safe house where we hit everything and our plan for a lot of these robberies were was that we would wait for about six months for the heat to die down.
And then we would take the goods up to Oklahoma where we pawned it off and take the cash and and use it to to party and everything else and as I go through this. Like that, that was who I was and that's that's all I cared about.
Lynne: Back then, Jason didn’t really have that much guilt about what he was doing. He says he just saw it as a job, a way to make money. He didn’t really see that he was harming people.
Lucia: But he feels really differently now.
Jason: I’ve relived that moment for the past 15 years of my life and even now talking over it. I'm in tears.
I was in a terrible place in my life and it doesn't excuse anything that I've done and I've lived my life after prison feeling like I have a debt to pay to not only my victims but also to society because of the harm that I've done in our community. And there have been nice where I've woken up crying because.
oui. Visions of what I did are just so vivid. I can still see the faces and I can still see. How we were and what we did. And it's heartbreaking and I feel immense amount of guilt. For forever changing their lives.
Lucia: While living in the JDC, Jason started to change. Something big happened.
Jason: So I became extraordinarily religious when I was in there. And so I started leading Bible study groups.
I started fasting. I became this religious nut inside prison and in my mind, I thought that if I was holier than thou that God would essentially allow me to escape this prison sentence and I would eventually go home and that was basically the premise that I use during my entire time there.
Lynne: Eventually, Jason’s court date arrives. But Jason doesn’t get released. He’s sent to a juvenile prison for 12 years.
Jason: I feel nothing. And I'm in the State of Shock in a wasn't until I got to my prison cell later on that night that I laid down and I just started crying my eyes out.
You know prison became almost like a time out to say Jason. Look at what you're doing with your life. And really consider if you keep going down this pathway we're going to end up and that was one of the big learning lessons I had while I was incarcerated.
III. Jason is in prison, finds God, and starts thinking of himself as someone who can teach others
Lynne: The way Jason tells it, he was a little different than the other inmates. He happened to be one of those kids who was well educated and well behaved.
Lucia: Also, he was Asian.
Jason: So the first thing is that I was the first Chinese person in the prison system in 10 years.
Lucia: He started working in the kitchen, cooking, and cleaning, and eventually earning the trust of some correctional officers.
Lynne: So they agreed to let him teach. The correctional officers let him have this group room every Sunday where he’d lead bible study and teach things like algebra to other inmates.
Jason: And so what I did was I ended up teaching Bible classes while I was in prison. But also taught GED classes and so I would help people learn math and reading and all these other things that order to achieve their GED and I didn't realize that the time but that was actually one of the best ways to gain respect because people start to realize well, hey, you know, Jason has value and people in prison are so hungry for an opportunity not follow in their parents footsteps and to not be this statistic.
Lucia: The way Jason sees it, the group room where he taught algebra and bible study—that room became a safe space from the toxicity of TYC.
Jason: We would have gained leaders inside these group rooms singing hymns on the top of their voices and and really, you know, it was just an amazing transformation.
That I really took as a learning lesson moving forward that yeah, you know you give a person a safe space to really apply themselves and to be the person that they want to be people want change they want transformation, but the current system just doesn't allow them to do so.
IV. Jason gets out of prison
Lucia: Jason eventually got out of prison. He was actually released after three and half years on good behavior and spent the next nine years on parole.
Lynne: What would you say is the biggest change that happened to you in prison?
Jason: I went to prison I did not take accountability and ownership of what I had done. I blame the world.
I basically blamed everybody else and I said that, you know, I didn't believe that I was the problem and. When I went to prison my mom she was still working a 12-hour night shifts, but I had hated my mom all the way up until I went to prison and when I went in I start to realize how much she actually loved me.
She would drive 14 hours every single weekend to come see me in prison for two hours. And when she showed up she would say even though you're physically imprison mentally or emotionally. I'm in prison with you. And everything the visitation my mom and my grandma they would break out in 10 years.
And what I started to learn was that I'm responsible for robbing them the thing I'm responsible for putting my mom through this hardship. I'm possible for putting myself in the situation where now I'm locked up in everything has been taken away. And so over time it didn't happen overnight over time.
I started to realize that I'm the source of my consequences and of my future in regard to realize that if I started changed some of my old life lot fees in the way. I view the world that may be one of the tools I can offer change my future because I would see inmates that got released. And would literally come back months later and I told myself I didn't want to become that.
V. The entrepreneurial talent locked up in prisons and how he got his company started
Lynne: Jason says that it’s this shift in thinking—that he was accountable for his own future—that really put him on the entrepreneurial path.
Lucia: Jason ended up joining Defy Ventures as an entrepreneur in training. He calls Defy the “shark tank for people with criminal histories.” The idea is that a lot of people with criminal histories already have many of the skills they need to excel at business, to be entrepreneurs.
Jason: For example when you look at gang. Means they have a board of directors. They have bylaws. They have a sales organization. They have Logistics strategies. They have wholesaling strategies. They have marketing strategies. They run in some cases with higher profit margins than then legal businesses.
And so we have so much of this entrepreneurial Talent locked up in prisons and when their release they really have no choice other than to Resort back to crime and I don't take that lightly because nobody should Resort back to Crime then when you look at the transition back to society and all the laws and requirements that are in place.
I don't regret any of my failures.
Lynne: Jason, though, went on to join the Defy Ventures program as an entrepreneur in training.
Lucia: Defy Ventures, by the way, hates the word ex-felon.
Lynne: Yep. At Defy Ventures, Jason got to go through a curriculum developed by Harvard and Stanford MBA professors and was given $30,000 to start his own company.
Lucia: That’s a pretty incredible opportunity. The company did run for two years, but it eventually failed, and Jason lost almost everything. I speak with Jason separately about his startup, which you’ll hear when we launch the premium side of the podcast.
Lynne: And even in all of this, Jason recognizes he’s one of the lucky guys. He got out early. He made connections. He was selected into this program, trained and handed funding.
Lucia: That’s not really the story for most people with criminal histories as Jason explains.
Jason: The current system in which we incarcerate people I think is the wrong approach because we essentially Warehouse people give them no educational training and they have a felony on their record and then when they're released their given two hundred dollars and basically a welcome back soon at the.
And so when you're released from prison, first of all, you have to find housing and you have to find a job and the problem with a lot of people in prison, especially if you've done significant time is that the type of you have no skills, you know, there's no training inside a prison or very rarely are there vocational training.
Lynne: Jason’s current company, Free World, is trying to solve this problem—to make it easier for ex-convicts to reintegrate into society.
Lucia: Jason actually got approached by Matt McSherry, a successful entrepreneur who really cares about helping prisoners find work. It was Matt’s idea to focus on the trucking industry.
Lynne: Wait, the trucking industry?
Lucia: Yep, trucking.
Jason: Now the reason that we chose the trucking industry is because in the trucking industry 80% of the industry is owned by Mom and Pop shops. And so they typically do not care whether or not you have a felony second of all the cost to educate somebody to get their CDL a license is extraordinarily cheap for trucking school it cost anywhere between 2,000 to 2,500 dollars and somebody can get their license within 30 days and when you get into the trucking industry.
You can start making about 50 to 60 thousand dollars right off the bat with many people actually going up to a hundred fifty to a hundred eighty thousand dollars a year. So that's the type of income progression that we have not seen in any other industry.
Lucia: Jason’s company’s business model is pretty smart. If they can help someone with a criminal history secure a job that pays at least $40,000 a year, they take 7.5% of their income for 2 years, and use that money to help the next person get a trucking license.
Lynne: Do we know how they’ve been doing so far?
Lucia: Yea, the company is pretty transparent about their stats. They have a total of 55 people who’ve graduated through their program and gotten licenses. On average, these guys have served time for 10 years and now make $56,000.
Lucia: So much of Jason’s own story—and what he’s doing with Free World—really challenges the stereotypes around Asian Americans, ex-convicts, and entrepreneurs.
Lynne: So of course, we asked him what rocking the boat means to him.
Jason: So rocking about what it means to me is challenging what we know to be true and learning from people that have been through it.
It's very easy to think that people that go to prison are terrible people that should not be trusted with jobs and employment and around your kids and all this other stuff in my experience.
I found the exact opposite to be true. These are men and women that truly want a legitimate chance at life. But unfortunately the system that we have today is such an uphill climb that it's incredibly difficult to break out of these cycles of recidivism.
Every person that comes into this world is born with a god-given gift and it isn't, you know, we always think about gifts as running and singing and Athletics and all this stuff, but maybe you're the best maybe the best chef that you know, or maybe you know how networked or maybe know how to, you know, anything out there right?
Maybe you're a great writer. You're born with a gift and you have self worth. The second thing is forgiveness. You know, you don't have to physically be in prison to be in prison. Many of us put ourselves in mental and emotional prisons because we haven't chosen to forgive ourselves.
We haven't chosen to forgive the people in our lives that have done us wrong. We haven't forgiven our past mistakes. So I would recommend forgiveness being able to look at yourself and say you know what, I forgive myself I forgive myself for lying to my kids. I forgive my father for abusing me. I forgive my best friend for for lying to me or or not being there when I needed them.
And when we start to forgive ourselves a whole host of opportunity start to open up a lot of doors start to open. So the things I've been really powerful in my life.
If you are interested in finding out more, check out Jason's company, FreeWorld.
Additional organizations that provide training:
Defy Ventures provides training and mentorship to convicts and ex-convicts.
Help for Felons lists reentry programs for ex-offenders.
Follow Jason on social media: