Josh Estey/AusAID [CC BY 2.0 (], via Wikimedia Commons

SPECIAL GUEST: Ryan Ryskamp. From mandatory minimums to tough on crime initiatives, our politicians have spent the last 30 years in an ongoing escalation against crime. Today we are statistically safter than we've ever been. And yet, the US now locks up more people than countries such as Iran, North Korea, China, and Russia. Many of those behind bars seem caught up in the war on crime despite non-violent or minimal offenses. Perhaps it's time we rethought the way we're handling the problems facing our society, and take a tough look at our tough stances. In this episode, we're joined by someone with personal experience of just what the criminal justice system can, and cannot, do. We hope you'll join us as we rethink the criminal justice system. Recorded 8/18/2015.


You can download the episode here, or an even higher quality copy here...


Mike & Matt's Recommended Reading:

Ryan's site,

Ryan on Twitter

OpportunityOf on Twitter

Mission Launch site

Mission Launch on Twitter

Rebuilding Re-Entry site

Rebuilding Re-Entry on Twitter

The Prison Crisis on

More coming soon...



Alpha: Welcome to another episode of Robot Overlordz, episode #199. On the show we take a look at how society is changing, everything from pop culture reviews to political commentary, technology trends to social norms, all in about thirty minutes or less, every Tuesday and Thursday.

Mike Johnston: Greetings cyborgs, robots, and natural humans. I’m Mike Johnston.

Matt Bolton: And I’m Matt Bolton.

MJ: And joining us on this episode is Ryan Ryskamp. Ryan, thanks for joining us.

Ryan Ryskamp: I appreciate it. Thanks guys.

MJ: Our standard question that we always ask guests, for people that maybe aren’t familiar with you or your background, when you’re meeting someone for the first time, how do you kind of sum up your background for someone, giving the high-level view of what you do and a little bit of what you’re about?

RR: So the work that I do, I’m like part entrepreneur, part social justice non-profit employee, or that’s kind of my passion, is delving into the criminal justice system and trying to help get people back on their feet after re-entry. And the reason why is because I was convicted of a federal criminal and I served three years myself in a federal prison.

MJ: Okay, so fair to say that you’re pretty up on the topic of criminal justice reform.

RR: Yeah, absolutely. And I don’t necessarily lead with that. So, I guess you asked me what I would tell someone. There are actually times when I say—if I’m in the right setting, I will tell people I went to prison right away, and you’d be surprised at how many people actually listen to you. I thought it would be the complete opposite, but people are actually pretty intrigued about it.

MJ: Yeah. Well, I think more and more people have had the experience, unfortunately, of that kind of thing, considering how many people this country currently has in prison and sort of our stats compared to the rest of the world.

RR: Yeah, I think you’re right, for sure.

MJ: So you’re also an entrepreneur then, correct?

RR: That is correct. That’s actually how I came across the organization that I do a lot of work with. I was an entrepreneur prior to prison, not just in the legal sense. I went for a non-violent drug crime, but I also had a legal business, and tried to kind of build that up when I came out and ended up in a coworking space trying to run a Kickstarter campaign and met two individuals, one who had been to prison, and her daughter, who was the CEO of the organization; and just found a really nice home to kind of try to make my mark and give back something, ut also a way to make the situation and my story work for me rather than just have it be a blip on my record.

MJ: What would you say that people maybe haven’t had an experience with the criminal justice system, sort of your average person who thinks anyone in that system—they’re bad people, they’re evil, they deserve punishment or whatever—what do you think your average person just doesn’t understand about how that system works and maybe what it means to get caught up in it?

RR: It’s interesting because I was actually just talking to someone today about how I’d gotten into what I’m doing. I think that everyone is going to have a different take on it, everyone is going to have a different experience; some people are going to be in higher institutions, lower institutions, some people are going to look really scary, some people are going to look really normal. But when it comes down to it, I can almost guarantee the “normal” person that’s never been in touch with prison is that if every one of their family members or every one of their friends were honest, there would probably be a two or three-degree separation between them and someone that has gone to prison. And I would like to think that most people, if they really dig into, they know someone that’s gone to prison, whether or not it’s been revealed yet. It’s just one of those things that people don’t really talk about. You know, when I went to prison, I didn’t know anyone who had gone to prison. But when I came out, I found out that actually I was closer to some people that had been to prison than I had originally thought. But no one cared to tell me until they knew that I had been through a relative situation.

MJ: Do you think that silence in general is starting to change, and that people are starting to talk about this more or get more interested in it? I mean, as the numbers of people in prison have skyrocketed and it does seem like, like you said, most people are only really two or three degrees away from someone that’s had that experience, do you think that finally some of the silence around that conversation is starting to break loose?

RR: I think it’s starting to. I don’t think it’s necessarily gained its legs that its should, as of yet. I think that’s one of the reasons why the organization that I’ve put a lot of work into has done really well in a short amount of time, and that I’ve been able to kind of gain some attention, but also people listen to what I have to say. Because I don’t think it’s very common that someone necessarily comes out and says, “Yeah, I’ve been to prison; yes, I’ve changed my life around, or my actions, and the world hasn’t ended for me and I’m actually doing okay, and I’m just trying to be a person in society again.” I kind of equate it to—you know, if you look at the trajectory that the LGBTQ movement took, whereas I think prior to I’d say like 2000 and the ‘90s, it was a sin, an utter sin to be gay. And afterwards, after about the 2000s, something shifted in the way that they marketed their campaign and all of a sudden it just turned out that it was actually pretty bad if you were homophobic. And the way I think they shifted that is they just really encouraged anyone who was gay to come out and say, “Hey, yeah I’m homosexual. No big deal, still your friend, still your brother, still your sister,” whatever the case may be, and I think society found that the floor didn’t fall beneath anyone, everything was fine, hell didn’t open up. It was a big eye-opening moment for loved ones and friends and acquaintances that these normal people that they liked and they hung out with a lot actually just had a different sexual orientation. It wasn’t anything that they could logically say, “I shouldn’t be around you anymore.” And I think that is going to be the same way that anyone who’s been to prison with a criminal record, they’re going to have to speak up and that’s going to be the way that we reduce the stigma that’s associated with having gone to prison or having a criminal record.

MJ: So, I don’t think we’ve actually mentioned it by name yet. What is the name of the organization that you’ve worked with? And, I guess, could you high-level sort of a little bit their mission, so to speak?

RR: Yeah. So I came back and I met these two individuals and they work for an organization called Mission Launch. It was a mother who had been to prison and a daughter who was fed up that her mom went to prison. And we began working together; I volunteered with them for roughly about six, maybe about nine months, and then they took me on as a fellow. It was specifically an entrepreneurial fellowship where they were helping me navigate kind of the obstacles and the pitfalls that could occur while someone’s on probation that had just come out of prison, and were helping me to build a business. And so we have built a small business with that and I’m doing branding and design, entails things like web design and graphic design, things like that. But I’m really starting to get into some nice clientele that want to do some brand development and brand management. And that’s all because of them; that’s all because I worked with this organization and they put me through this fellowship. I still do some volunteering with them these days, but recently publicly the SBA came out and they awarded them $50,000 to start an accelerator. At this point, I’m excited to apply for the accelerator and I’m excited to get in there and try to be the first one in the program so they can help me build the business up even higher. And it’ll be the first accelerator, to my knowledge, for anyone that has had a criminal record in the nation.

MJ: Is that Rebuilding Re-Entry?

RR: Well Rebuilding Re-Entry were some hackathons that we did. We did some hackathons centered around coming out of prison and essentially rebuilding re-entry, and easing the re-entry process, and had a lot of success with those; those were a lot of fun.

MJ: Actually, one of the things I found fascinating…after we communicated with you about kind of coming on to talk with us—I took a look at your website—so that’s, correct?

RR: Yeah, so Opportunity Of is—I’ve been kind of going back and forth—but Opportunity Of is what I hope to turn into part me using my professional expertise, branding and storytelling—because I’ve had to take a story that is pretty colorful but isn’t so easy to hear for some people, and I’ve had to be brave enough to come out there and tell it my way before anyone else gets the chance to tell it in a way that I don’t see so favorable. So doing this, telling the story over and over again, I’ve kind of become addicted to storytelling and branding, re-branding an individual, and Opportunity Of is kind of a place where I can put all those ideas down. Soon I’m migrating over my things from, which is the freelance business that I run. I’m going to look towards building I guess more of an agency, if you will. I’m going to hire some employees once we get into the entrepreneurial program, the accelerator, and try to turn it into a full-blown branding firm, and it will all be under the name Opportunity Of.

MJ: What are some of the big things that you learned about your experience? I know you’ve written a little bit on your Opportunity Of site, about the experience of learning in prison and what you make of that learning actually being a bigger deal than actually learning. I guess I’m curious to hear a little bit more about what your experience was like as far as the things maybe that you learned and the things that that might hopefully launch you out into now that you’re, you know, sort of back in the world.

RR: Yeah. So, I think you go to prison and really it’s just an extended vacation. You can take it however you want to. Sometimes you don’t go to a very nice place, sometimes you go to a place that’s not so bad. But when it comes down to it, the scariest thing isn’t anything that you’re going to see on MSNBC “Lockup,” “Gangland,” anything like that. The scariest thing is just kind of being alone with yourself. You have to really confront yourself and figure out who you want to be, because otherwise it just gets kind of boring. And there’s things you can do to pass the time, and people certainly find ways to pass the time without having to necessarily have a couple serious conversations with themselves to figure out if they want to be involved in this cycle anymore. But you have so much time on your hands. I mean, before I went to prison I went to James Madison University, graduated with a Bachelor’s degree. I learned more in prison than I did in college. I did it because I wanted to. I asked for books instead of asking for money; I would give personal training, because I was a personal trainer prior to going to prison, and I would trade that to some of the guys that needed it and wanted to learn how to workout for their expertise in business. There were certain people there that had made a lot of money and been successful and had powerful positions, and I hadn’t necessarily met very many people like that before.

MB: Do you have any thoughts on—I don’t know if I’m jumping ahead here or not—but once you got out…I know the recidivism rate, and you even talk about it, it’s extremely high in this country, most people going back to prison. Can you talk a little bit about what it was like for you after you got out and why you think, based on your personal experiences, why that is?

RR: Yeah. I mean, you’re absolutely right, the recidivism rate sucks. It’s a big just right-in-your-face stain that the United States has to deal with and it looks really, really terrible to other countries, and it is terrible. You know, the way that I see it is you have so much energy built up right before you come out, and they try to do things to dampen that. That put you in a halfway house, which is supposed to be a transitional period. To a certain degree, it does work; your spirit does get kind of beaten down a little bit. But what it really comes down to is you take freedom away from someone for so long and you give it back to them eventually, once they get their freedom back and they kind of get over their little jitters and things like that, they still have that energy. You’ve got to figure out something to do with that energy. You’re creating these people and not providing them any rehabilitation. You’re just kind of giving them the opportunity to rehabilitate themselves, and that’s what it comes down to. There’s no real class structure or foundation for programming or anything like that that happens, at least there wasn’t in the federal bureau prisons, that was really worth a shit. Everything was a joke. When it comes down to your release, you’re the same person you were before unless you’d made a decision not to be that person anymore. So, the recidivism rate of course is going to be high, and higher than we want it to be, because there’s really nothing recurring during the time you’re away that is trying to make it any less. The only thing that I can see that really is going to make an exponential impact is entrepreneurship. If you take someone that has that energy and has that motivation, they’re hungry, they want not only money, they want purpose and they want status, they have kind of all these things that really successful entrepreneurs tend to have; they’ve got a high tolerance for risk. If you give them the tools necessary to build a business, they’re going to do it, and they’re going to do it and they’re going to feel sympathetic and empathetic to the cause for some of the guys that don’t necessarily want to build a business that have come out of prison and there’s going to be a trickle down effect. You’re going to have one guy that might employ 20, one guy that might employ 2, one guy that might employ a thousand one day, and he’s going to be really, really sympathetic to someone that comes in and says, “I made a mistake and I have a felony because of it, but I want a chance, and I want to work, and I want to provide for my family.” Right now, we’re relying upon people that have been kind of just screwed up by this stigma that occurs in the country that someone that comes out of prison should not get a second chance.

MB: Yeah, I always thought that that was—I’ve never been to prison, so I can’t speak obviously for that, but it seems like you broke the law, fine, you went to jail, okay, but then you get out and it’s like you can’t escape it because there’s that box you have to check on any job application, and it’s almost like wearing a scarlet letter around. To me it almost seems like, well, if the only job I can get is some low-wage type of warehouse job or whatever, you kind of start seeing why people turn back to crime and back to doing the things that they did before just because it pays better than, you know…

RR: Right. And when most people are triggering the recidivism number, they’re not even committing new crimes. And if they are committing new crimes, very few of them are really of the same nature that they went to prison for. A lot of them and the vast majority are probation violations, and you’re stuck with this system that is very, very stringent. I’m technically not allowed to hang out with other people or associate with other people that have a criminal record, a felony. If they have a misdemeanor, it’s okay, but it’s frowned upon. But if they have a felony, I’m not supposed to hang out with them. I had to get approval from my probation officer to work with the non-profit because the vice president has a felony. When you’re talking about coming out, another huge thing: when you come out, you are emotionally, mentally a different person, and you’ve been through different stuff. Your family hasn’t been through it. So, when you kind of freak out a little bit because there’s too many people in a public place and you just don’t even know why you’re really freaking out, you know, it’s hard to reach to either your wife or your mom or your dad or your brother, or your friend even, if they haven’t been in the same situation. You kind of sound like a whack job, and that kind of occurred to me. Like, you know, I still, whenever I hear keys I get a little freaked out. I can bring myself back really quickly, but that was one of the things that would signal—like the guards, the guards would wear keys, and they clanked wherever they went. So the nuance of the sound brings you back to that place, and you almost for a second have to just tell yourself like, “You’re not in prison, you’re not in prison, you’re not in prison.” But I found a lot of solace in being able to talk to the vice president of Mission Launch because she had been through what I had been through. And she was two years ahead of me, so she had gotten out—or maybe a year ahead of me—and she had gotten out and kind of started to get herself back on her feet and knew all of the stuff that I had gone through, and she’d even kind of alert me to some of the other things that came ahead, and that was priceless. That was one of those things where we might look at someone and think like, “Well, that person just started not to care and they just started to do whatever.” It might not be that simple, and maybe they legitimately had PTSD and just couldn’t handle being back in society. If you imagine someone goes to prison for 10 years, 15 years, 20 years—I mean, they’ve spent their whole entire lives there, that’s all they know, and that’s hard. For anyone to do that, it’s hard; for the military, it’s hard; there’s suicides every day for veterans. And not to say that I know what it feels like to have PTSD as a veteran, but I certainly sympathize with what they have to go through and I think it’s something that one day we’re going to figure out that we’ve probably caused PTSD to the people that we’ve sent to prison as well.

MJ: Ryan, I think we’re kind of talking around a little bit the whole issue of punitive vs. rehabilitative, and I guess I’d kind of like to pull that out. I know you’ve written about this because I was reading one of your articles on Opportunity Of—or actually, no, this was on Mission Launch—about the criminal justice system is a hostile system that mainly punishes people, I think is what you wrote. I guess for the people who haven’t been through it, how do you really explain to them that difference and I guess what would you say to them to make them think that maybe rehabilitation is something that needs more attention or more focus, or…I mean, I assume you would think that—and maybe this is an assumption—that rehabilitation would be more effective than just purely punitive. I think this was what Matt was really saying, and Matt, correct me if I’m wrong, that I think that punitive just seems like it doesn’t really—if all you’re doing is punitive, it doesn’t serve anybody.

MB: Yeah.

RR: Yeah, absolutely. I think the punitive nature just got out of hand. Obviously people need to be punished, the punishment needs to fit the crime, and there’s all these things. But what it really comes down to is we’ve kind of become the nosey neighbor, the guy that hates kids, or he just basically wants to be unhappy. Imagine that, that’s like the US government or society, and they’re just mad at you. They’re just mad because, you know, you sold drugs—I get it, you’re not supposed to sell drugs. But they’re sentencing you not because you’re a threat to society, like it was originally intended, but they’re sentencing you because they’re mad at you. They’re giving you sentences that are way above what you should be getting because they’re mad at you, and that’s a hostile system, that’s something that is going to implode upon itself. And I think we’re sort of seeing that a little bit, because I’m going to get off probation any day now because I’ve reached my halfway mark, and that’s not because they’re trying to do anyone a favor, that’s because they don’t have any money, and it’s bleeding the government that has all of this debt, and it’s become one of the biggest line items under “Defense.” And I think the main thing is we’re just putting people in prison because we’re mad at them. It’s nothing to do with public safety. It’s not like I would’ve ever committed even a jaywalking offense if you would’ve just told me that, “You’re seriously going to go to prison if you don’t stop this shit.” I would’ve totally stopped. I mean, I don’t want to go to prison. Who wants to go to prison?

MB: Yeah, that’s a good way to put it. I never thought of it as, “We’re just mad at you, so you’re going to go away for a while.” The other thing I think is that we seem to be handing out felonies for what used to be not as serious as offenses and now every politician, their entire answer to everything with crime is, “We’ll just make the punishment more severe,” or whatever. That seemed to be very prevalent in the ‘90s; the ‘90s, we got three strikes and mandatory sentences, which I’m very against—you know, that whole, “We’ll just take it out of the judges hands. He has no discretion; he can’t even look at the case logically. We just have to send this guy to jail for, it says here, for five years,” no matter how minor it was, or whatever.

RR: Right, which is amazing, right? Because the judge is the one who has probably been a prosecutor longer than the prosecutor has and then went into criminal defense and now he’s been brought up to the judgeship because they feel he’s well-rounded. That’s what you’re supposed to do a judge. But instead, they give it to the newbie prosecutor, who probably is just, once again, mad at you or just has something to prove.

MB: To me, it actually reminds me of, you know, you read all these stories about kids in school, and “Billy made a finger gun or whatever, so because of our rules we have to expel him from school, we don’t even have any discretion…” [laughs] If we’ve learned anything from watching politicians over the years, they’re not the brightest people in the world, and having them pass laws like this I think is…But I think you’re also starting to see now where that stuff—people are actually starting to stand up and take notice and going, “You know what? Hey, when we have more people in prison than places like Iran and North Korea, then that’s become a big problem.”

RR: Actually, and it’s funny you say that—it’s not funny at all, but I guess I can laugh about it finally—because I do a lot of graphics work, I do a lot with branding, but I do a lot of graphics stuff and we’re trying to brand kind of a campaign when I was working with the non-profit. And one of the things we found out was that there’s 36 states that incarcerate more people than any other country in the world—individual states per capita, part of the ratio of their population. That, to me, was crazy. Cuba was the next worst per capita, past those 36 states. But yeah, it’s become a terrible, terrible issue. What you’re seeing is the politicians…they’ve almost dug themselves in such a deep hole, and they see it. It’s one of those weird things, like they see the problem, whereas usually the citizens see it and they kind of dictate what the politicians should be doing. They kind of see the problem now and now they have to, like, almost spin the criminal justice thing in the opposite direction. Because if they don’t, the people don’t even understand the epidemic that’s going to ensue or the downfall that’s going to happen financially if they don’t do it. California had to let out I don’t know how many people because the conditions just got so bad, they kept stacking people on top of each other. And that happens in a lot of other places, too; I’ve been to some pretty bad jails. And the federal system has a lot of money, and you’re not really going to ever have to deal with the ACLU because your conditions are fine. But when it comes down to it, there’s instances all over the place that they are running out of money.

MB: I understand locking up rapists and murderers and that kind of thing, but I don’t want to have them get early release or not have them in prison because we’ve got to lock up somebody who was smoking pot or whatever. To me, that makes no logical sense whatsoever.

RR: No, absolutely not. Yeah.

MJ: Ryan, for people that maybe are starting to reconsider this whole notion of criminal justice and maybe have an interest in the issue, what advice would you give them to kind of start getting involved, maybe start the wheels turning on this actually becoming a much more focused on issue? It seems like it’s still—I mean, you get a lot of reporting on some of these stats—a couple of the sites Matt and I read I know cover the fact that we lock up more people than China or Iran or Russia. But I haven’t really seen that a lot on the mainstream media, particularly. How would you encourage people, maybe your average person, to get involved in this issue and to maybe start making the wheels of change turn?

RR: I think it’s a perfect opportunity, right with the elections coming up, to really start to push that issue on the candidates—which every single major candidate has already come out—I think besides Donald Trump, and maybe even he did it and was just an asshole in a bunch of other different ways—but every single one has come out and said, “We have to reform the criminal justice system, we have to stop locking people up at the pace we’re doing it at.” That’s great. What I want to see is I’d love to see people ask them the hard questions of, “Alright, cool. How are you going to do it?  How are you going to save the people money? What are you going to do with all the drug offenders? What are you going to do if you legalize marijuana? Is it going to be retroactive?” You know, really ask them tough questions that I’m sure they’re going to try and dance around, but if enough people ask those questions, enough people show interest, that’s when it’s really going to, one, validate their idea that we do need to reform the criminal justice system; two, it’s going to hopefully push it even further and get it to be one of the major topics that are discussed, and then it’s just that much more of a chance that something actually happens. I mean, there is actually a lot of bipartisan support for criminal justice reform. I was at a seminar about five months ago and I was surprised I saw Newt Gingrich there, I saw a bunch of some other Liberal politicians, Cory Booker. And these are people that, you know, if you would tell the average person that these guys are working together, they wouldn’t even believe you because they’re so far right and so far left.

MJ: Well, Ryan, thanks so much for joining us tonight.

RR: I appreciate it. Thanks Matt and Mike.

MB: Thanks.

A: That’s all for this episode of Robot Overlordz. Are you interested in the future and how society is changing? We’d love to have you join our community. Visit our website to learn more and to connect with others that share that interest. You can find us at RobotOverlordz.FM. The site includes all of the show’s old episodes along with complete transcripts, links to more information about the topics and guests in each episode, and our mailing list and forums. We’d also love to hear what you think about the show. You can review us on iTunes or email us.

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MB: Thanks.


Image Credit: Josh Estey/AusAID [CC BY 2.0], via Wikimedia Commons