From Prison To Programming

With Rick Wolter

From Prison To Programming

I believe that getting underrepresented groups into software development is a good thing. This is not a controversial opinion until you start talking about felons.

Today’s guest is Rick Wolter. He’s an iOS developer who served 18 years in prison for second degree murder. Rick killed somebody and for some that’s all they need to know about Rick. But today’s episode is about Rick’s path to redemption him, teaching himself to code in prison, smuggling in a Python interpreter, and then getting out and trying to get a job as a dev when you’re a felon.


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Adam: Hi, this is CoRecursive and I’m Adam Gordon Bell. Each episode is the story of a piece of software being built.

I believe that getting underrepresented groups into software development is a good thing. This is not a controversial opinion, lots of people feel this way unless you’re talking about certain groups like felons.

Rick: Like you can legally discriminate against a felon, legally. You can say I’m not going to give you a job because of who you are. And so, this is a different group and it’s not the most popular, right? I’m not saying I deserve your compassion. I’m asking for it, I’m asking for you to give me the chance but I’m not saying I deserve it.

Adam: That is Rick Wolter and he’s an iOS developer. And he gets why people might not want to give him a job but is it fair to judge somebody just by the worst thing they’ve done?

Rick: You can’t overlook when the worst thing is actually the worst thing and I have the worst thing you could do. It’s not like he killed somebody, people literally say that and refer to what I did, they refer to the worst thing.

Adam: So, yeah, Rick killed somebody and, for some people, that’s it, that’s all they need to know about Rick. But today’s episode is about Rick’s path to redemption. Him teaching himself to code in prison, smuggling in a Python interpreter and free code camp lessons and then getting out and trying to get a job as a dev when you’re a felon and then, finally, trying to help marginalized folks learn development. It’s a wild story and it starts when Rick was a teenager and his dad got a house.

Before Prison

Rick: Up until then, we had stayed in little trailers and, at one point, it was a really busted trailer that didn’t have rooms, it was just beds on each end. We were able to get a house and you couldn’t tell us anything. I thought I was rich, I thought we were living the life.

Adam: That house was just a happening place.

Rick: It was like there’s always extra people there, we were always either doing some drugs or alcohol. It was just very, very dysfunctional. I was into selling drugs, I was into whatever, I just made the worst choices you could ever imagine in life up until that point, in and out of county jails and juvie and all the things. I had gotten into a lot of altercations and they always ended in fights and violent incidents. I didn’t think I was a bad guy, clearly, I wasn’t making great decisions but I wasn’t the aggressor usually so I usually felt like it was justified or you just rationalize your behavior and, when you’re that young, you don’t know any better.

And again, this isn’t minimizing it, but I was raised you don’t walk away if someone says something, you’d never let somebody punk you. It was just one of those things, it’s embedded in you at a young age, it’s really hard to break.

The Fight

Adam: One night, everything changed.

Rick: At this particular time, me and a friend were at a party and a big fight broke out and my friend started getting jumped, it was some older men from our area. We were teenagers, he was 17 and I stabbed one of the guys. It was just a horrible decision, I was an idiot, just a really dumb kid. Guy I stabbed was 28.

Adam: So, Rick fled the scene of the fight before the cops could arrive.

Rick: Someone called me, he was a friend of mine and he was crying because the cops had picked him up and I could tell he was crying. I’m like, “What’s wrong with you?” He’s like, “Dude, you got to get out of there.” He’s like, “That dude died last night. The cops told me they’d give you self-defense if I told them.”

So, basically, he was telling me he told but he also was trying to give me a heads up to give me a chance to get out of there. I probably need to look at statute of limitations before I start talking too much. So, yeah, I took off and hid at some people’s houses and some friends’ houses.

Adam: Hiding is probably not the responsible thing to do but it hadn’t really sunk into Rick the gravity of the situation. Although, he did know he needed to talk to his dad.

Rick’s Dad

Rick: And so, I called him and I’m like, “Hey, Dad, you probably need to come over.” He said, “I’m getting calls that cops spread at our house. What’s going on?” blah, blah, blah. And so, I call him and he comes over to the house and I’m like, “Man, you need to sit down.” He sits down on this bed and I mentioned my dad who is very loving, very dysfunctional in his own right. He’s got stories that, dude, you wouldn’t believe him if I told you. It’s stuff you see out of a movie, stuff that happened years ago. Just to give you an idea, he named me after his best friend who, their whole group, one died in cop shootout, shootout with cops, the other OD’ed and the other … Yeah, the guy, his life is like a movie, it’s pretty wild.

He’s a real big dude, too. He’s 6’5”, 260 at the time and I remember standing there and I was like, “Dad,” and I had been in a lot of incidents and he’d been, in his dysfunctional way, to pride in it sometimes. “Oh, yeah, my boy stands up for people,” or, “Rick got a fight and won.” So, this very toxic my boy could fight type of thing. So, there were many times where we discussed that stuff and he’s not a normal parent, he would laugh and hear about these tales. And so, this is one where it was just sad. I was like, “Man,” I said, “I stabbed somebody last night.”

And he’s like, “Oh, no.” He said, “How is he?” And I’m like, “Well, that’s what I’m trying to tell you, Dad.” I’m like, “The guy died,” and he just broke down in tears and he sat down on the bed and he just dropped his head and just was bawling. This is a really big dude, wild, everywhere he goes is a big party type of guy. To see him just breakdown like that, it was super sad.

Adam: Do you think your dad was crying because he knew you were going to go away?

Rick: Yeah. Oh, he knew. I didn’t fully know but he knew. You could tell he knew like, “Oh, yeah, you fucked up this time. You really messed up this time.” We lived a life that was pretty wild and, at some point, it does catch up. And I think, at that point, it caught up with it because, after that, especially for him, it was downhill. Fell back into addiction a little bit later, lost a lot of stuff.

Entering Prison

Adam: So, Rick turned himself in, he was charged with second degree murder. He took a plea bargain for 21 years and he would end up serving almost 18 years in prison. At first, prison was a culture shock for Rick.

Rick: I think I was at ACI, Apalachicola, which is a notoriously hard prison, it’s up in the Panhandle of Florida. It’s not even the rest of Florida, it’s weird. You get up there, you feel like you’re in Alabama. It’s wild, it’s so different from where I’m from. And no offense to anybody from the country, but I’m just saying you got these stereotype of spitting tobacco, come here, boy, get your ass over here, boy, literally on horses with shotguns at the time, it was wild.

Adam: Really?

Rick: Yeah. At the time, they had this thing, it was a literal chain gang. It was something out of a freaking movie from the ’50s or something, it was just wild. Your life could suck in there depending on the job you get and you might get … One of my first jobs, it was a cabbage field, I think. You’re just out there freaking picking cabbage and doing farm shit and that was horrible in the Florida sun all day. Man, it sucked. Yeah, it was terrible, it makes your time way worse, way worse.

Adam: Prisons can vary a lot but, in Florida, they mainly have a dorm system. Prisoners sleep in a large dorm room and there’s no air conditioning so it’s pretty humid most of the time. The first big challenge Rick had in prison was finding a way out of cabbage duty.

Rick: Can you imagine 18 years of picking cabbage? I can’t put that on my resume, right?

Adam: Rick applied for other jobs.

Rick: I usually tried to get in jobs where it would just have extra free time so that I could read. I was always either running the education department or a houseman job which is you just clean the dorm after everybody leaves.


Adam: Once he got off the chain gang, Rick did just fine in prison. And he’s an outgoing person so he actually had lots of people who’d come and visit him. You could only have so many people on your visitor’s list though.

Rick: So, I put my buddy Jared on this other dude’s list, Dan, and we’d get up to visitation, all of us together. And somehow, we say Dan’s name, we call him Dan the freezer man. Eventually, my friend Jared’s like, we went to get a drink, he’s like, “Rick, come here.” And so, we’re getting drinks and he’s like, “Why do you all call him Dan the freezer man.” And so, I tell him, I’m like, “He buried somebody in a freezer.” And he’s like, “Bro, what the fuck?” He said, “Man, take me off dude’s list.” He’s like, “Put me on your list, don’t ever put me on somebody’s list like that ever again.” And I’m like, “Ah, maybe I should have told you.” He’s like, “Yeah, you should have fucking told me.”

Adam: It’s weird though, I think it ties into your story, too. When you think of somebody with some label, this is what they did, it’s different than knowing the person. It becomes a thing they did but there’s other things in there, too.

Rick: Yes, yes, you separate it. I think you start viewing them as a human that have flaws. At some point, it’s almost like it’s an afterthought, you don’t even think about it.

What Do People Get Wrong about Prison?

Adam: So, Rick is going to get interested in software development while in prison and he’s even going to get a Python interpreter smuggled in so he can learn Python. But before we get into that, I’m just curious about what doing 18 years in prison feels like. What do people get wrong about prison life?

Rick: What do they get wrong about prison? I don’t think that it’s as hard as people think it is. If you’ve ever been to rougher poor neighborhoods, it’s like that, it’s basically the same thing. It’s no different except you can’t get away, you’re trapped. And I think that you maybe wouldn’t suspect how much fun you can have. You end up with friends and you have birthdays in there and you do have some fun.

Adam: When you say it, it’s like, yeah, of course you’d have some friends and you guys would hang out and there’d be fun but that’s not what makes it into the TV shows.

Rick: It’s not the fascinating part to people. If you went in, you’d be fine, just stay on your book and read or whatever. If someone as outgoing as I am can be all right, I think most people can be.

Adam: Nice. There’s a big lesson. Prison, not so bad.

Rick: It’s bad in the ways you don’t suspect, that’s the problem. You see life going by and you can’t do anything, you can’t act on it. There’s lots of going on, you want to do something. I got in boxing when I was in there and it didn’t matter, I can’t go pro.

Adam: Yeah.

Rick: You’re stuck in there. You could study whatever you want in there all day long, do whatever you want and you still, at the end of the day, you’re just going to land your bunk and you’re not going to be able to do anything with it. And so, that is maddening and in its own ways.

Adam: Eighteen years in prison can give you a lot of free time and, for Rick, a lot of that time was spent reading.

Rick: You don’t have responsibilities, really. You’re going to be in this dorm maybe because it’s raining and you’re going to read. I was super lucky, my brother, dude’s a fucking genius, honestly, and he’s constantly sending me something, just interesting stuff, intellectually interesting type books and he’s actually a professor now at Auburn University. And so, he would always look out for me and make sure I had stuff to read and it could be anything. I went through phases, phases of reading the classics then you go through phases of stuff about thinking like How Not to Be Wrong by Jordan Ellenberg or Blink by Malcolm Gladwell, I read all his stuff. But you have time so you can read even weightier stuff and it’s fun.

Finding A Skill

Adam: As Rick got closer to the end of his sentence, he started thinking about what he would do once he got out.

Rick: What can I do that can actually give me a decent life, where I don’t have to grind. And growing up, I did a lot of physical labor with my dad. He did sea walls and that stuff is brutal.

Adam: These were rock sea walls, rocks would get dumped in with front end loaders but also needed to be rolled into place. Rick’s dad was always looking for more help.

Rick: We might have a bunch of people stay at the house and the next day he’d be like, “Come on, you all, get up. I’ll give you all a little something,” so he makes us all go to work with him. But regardless, it was very impressionable on me that I don’t want to fucking do that the rest of my life, it was really hard. And so, I’m looking at skills and I don’t know how to do anything, I’m not mechanical. I’m like, “Man, this is going to be rough.” So, I think I was reading it in The Economist the demand for software engineers and as this was 2015, ‘14. And after I read it, I felt like everything I picked up had something about that.

So, before I ever started coding, I was having stuff sent in about coding. So, I would read all about it, I’d have books like I think it’s called More Awesome Than Money, it was a Facebook alternative startup thing. And I saw The Social Network, the movie, I don’t know, something about it was fascinating. And of course, it was more the idea of it rather than the actual thing because getting the hardcore skills is a lot different than just fantasizing about, oh, I’m making a ton of money as a coder.

Adam: In The Social Network, they’re coding and doing shots and then cannonballing into a pool, if I recall.

Rick: Right, it was my language. It was speaking my language at the time. I was like, “Ah, look at this. This is how everybody lives, it’s like the life of a king.”

The Computer Lab

Adam: So, now, Rick just has to learn how to code. Learning to code is actually hard but it does seem like a great thing to teach prisoners in prison if they’re interested but there’s a problem.

Rick: This isn’t California, this is Florida, they want you in the cabbage fields.

Adam: There is, however, a computer lab in one of the dorms.

Rick: They weren’t ancient but they were old Dell towers that you would see in a classroom in ‘98 maybe or ‘96 or something, just the older types of things. You could probably just look up any room with computers from the ’90s and it’s probably what it looked like.

Adam: These computers were part of a drug treatment program.

Rick: So, my friend Mohammad ran this dorm, I brought this to him, I said, “Hey, I’ve read about this stuff over here in this article,” and blah, blah, blah and I’ve had blogs sent in. I’m like, “I want to put Python on the computers in there.” And so, he’s like, “All right,” he’s down for it. So, we had Python snuck in on a thumb drive and we put them on the computers.

Adam: But how did you sneak it in?

Rick: Well, there’s lots of ways. Guards bring stuff in if you’re cool with them, you could do lots of different things. But this one in particular, we just knew somebody that worked there who wasn’t a guard but he did work in a different area. He’s passed now, he actually doesn’t work there, he passed away a little while ago. Awesome man though, really awesome guy. He’s the type that he just wanted to support people doing good things and he didn’t care if it was breaking a rule and he knew us. At this particular camp, I had spent almost a decade there so these people watched me grow up there.

Adam: Yeah. So, you got Python started up and then you type one plus one or, I don’t know, what happens? What were you doing?

Rick: Well, I got some books, it was a set and my brother got it to me and I just went through that book. And it was mostly foundational type stuff, this is what a string is, this is what this is, this is what a data structure is and, yeah, I was stepping through it. And then I tried different courses, we got access to MIT OpenCourseWare and I was watching, I think his name’s John Guttag, if I recall, this is a little while ago. I think he’s the professor of the MIT CourseWare for Python which was an introductory type of computer science class. I would follow that, I didn’t really understand a ton of it at the time. I’m not going to lie, I’d listen and, half the shit dude said, I was clueless about but I was trying to follow it.

You got to think about it, I was like a caveman at this point. I’m like a caveman and I’m trying to make sense of what these wizards are talking about. And then there were some that we had the Bucky tutorials and this guy’s got very down to earth just almost silly tutorials but I liked them. They were like, “If you got 10 tunas inside this array, then you eat one tuna,” real goofy stuff but, I don’t know, it spoke to me. Maybe it was because it was layman’s terms and so I was like, “Ah, I get it. Okay, I fucking get it. You haven’t got no tuna left, I get it.”

Adam: Yeah, a Python, I don’t know, that seems perfect. It seems like that’s exactly what I would maybe choose for you if I got to pick.

Rick: Looking back, I think you’re right. I stumbled onto it but I think you’re right. It’s a perfect building block. Just starting with something easy, with minimal syntax and you just learn, at least for the basics, learn what data structures are and learn control flow, that kind of stuff and then you can move on. It was a lot of fun and I used to lose myself in those Python problems and those YouTube videos that we had on the thumb drives. Yeah, it was a whole lot of fun and it was like an escape. We had a little bit of music on those computers and so you’d sit down and I would just zone out and just code for a little while. I still didn’t really know what I was doing, I didn’t find out till later that I was like, “Wow, I didn’t know a damn thing.” In my mind, I was a software engineer, it sparked that interest.

Teaching Programming in Prison

Adam: So, you might notice, from what you’ve heard from Rick already, he isn’t really a keep it to himself type of person. He starts talking about computer programming, he starts teaching his friend Ryan about computers and then, eventually, they start teaching a class.

Rick: So, Ryan starts helping me. I’m sure he would love to be here to say this, he’d be like, “You didn’t do anything.” It’s not that I didn’t do anything, it’s that he taught better, I felt. So, when I got him teaching, I just quit. I didn’t quit, I just started doing my own thing. So, he would teach the classes and I would code Python over on the side once I got him teaching. In his perspective, I duped him, I lured him into teaching and doing all the work but it was fun, we both had a blast.

Adam: But this whole thing was still a rogue class. These computers were supposed to be for some drug treatment program, not for programming Python.

Rick: That was the problem was that, when we started teaching the class, it was too noticeable and that’s what brought the downfall. If I just sat in the corner and done my thing, I probably wouldn’t have even been found out. And then coding books started coming in and they would approve some, they were very arbitrary depending on who’s working in the mail room. Someone got turned in to security like, “Hey, what’s going on here?” They just didn’t know what we were doing, they didn’t understand it.

Adam: It’s not a high trust environment.

Rick: Definitely not. We don’t even have metal forks and spoons. They think of movies, they picture us hacking everything and stealing money out their wallet. We weren’t even connected to the internet or anything. I understand why they wouldn’t trust us and it’s Florida, you don’t have those kinds of programs. This looks like a group of hackers, basically. Literally, we’re just trying to get skills for when we got out just to be contributing members of society, just normal people.

Adam: Yeah.

Rick: But when the word got to the warden and to some of the higher ups and so they came down on us. Well, not on Ryan, on me because word got back that I was the ringleader of this thing and they transferred me but I got a taste. That’s all I needed was that taste. I’m an easily excitable guy so it’s not hard to make me think like, “Oh, this is the best idea ever,” and I was dead set. I was locked in, I said, “Man, this is it,” and I had a totally inaccurate idea of how long it was going to take me. I thought I was going to get out and raise a Python code and get hired and, three months out, buy my mama a house and it didn’t work like that.

Getting Out

Adam: So, Rick got out and he found a place to live.

Rick: So, I ended up with a place almost incidentally. One of my friends who had been riding and visiting, her and I got really close and eventually became a romantic couple.

Adam: While Rick was in prison, Rick’s dad had fallen on some hard times.

Rick: He had lost everything, it was real bad, addicted to opiates and was staying at this dude’s house who was a known addict, known crack addict. With the help of my brother, we got him help and got him out of there. He’s doing fine now, thank God. Yeah, it was bad.

When I get him out, he starts working, trying to get jobs here and there. He doesn’t have a business anymore but people knew it from back in the days and so he would get jobs here and there. When he would, he’d call me and so I’d go with him. There I am back to doing sea walls, in the same thing I didn’t want to do.

In my spare time, I was doing just a two-year degree for programming at the local college. You don’t learn a lot there, let me rephrase that. You do but it’s a slow track. There’s so many classes that were just bullshit. Now, I look back I’m like, “God, I couldn’t condense that class to something way better.” And then after that, I enrolled in a CS program, transferred from there to Florida International University which is a state uni here.

Panic Attacks

Adam: This is where things can fall apart. It’s one thing to imagine being a developer when reading some exciting book about the creation of Facebook, it’s another to be out of prison, be doing manual labor during the day and then trying to build up a skill set at night.

Rick: I had panic attacks out here. I didn’t know what it was at the time but I was driving and I felt cold, super cold and dread and I’ve never felt this way, it was so weird. I turned the radio off, tried to limit stimulation, I almost had to pull over. What the fuck’s going on, is this a heart attack? I’m like, “I’m too young for a heart attack, what is this?” Later, after talking with people, they were like, “No, dude, I think that you had a panic attack.” So, oh, okay, interesting. This is something I wouldn’t expect especially because I’m very carefree, very rarely do you find me stressed.

Adam: Rick’s plan could have fallen apart at this stage but he started finding ways to hang out with software developers.

Rick: I just would go to these meetups and, all over Orlando, wherever there was programmers, I would show up and listen and didn’t know what was going on really but I was trying to make it happen. And it took a long time because I didn’t know anyone, I didn’t know a single person, didn’t know any programmers, eventually built some friends and relationships. I’m asking developers for time and advice and there are so many that were cool about that and would, “Yeah, what do you need? What type of help?” It’s just the awesome industry full of amazing people. And so, I would ask, “Hey, you want to grab lunch sometime? Let’s grab lunch.” That way, I can just basically ask them a thousand questions, it’s all it was. And sometimes I’d joke like, “I’ll trade you prison stories. I got a gazillion prison stories. I’ll give you prison story if you’ll give me information on how to become a programmer.”

Lunch With A Dev

Adam: One person who agrees to go to lunch with Rick and is still his friend today is named Ben.

Rick: So, I’m super broke and I got this truck that’s so busted. The truck, you see it, it doesn’t look like it even runs with the bent up ass, it’s red too like red Coke can on wheels. And so, I meet him for lunch and we come out and, Ben, he’s been a programmer for a long time so he is doing well and I insist on paying his lunch. I insist on paying it because I feel like this guy’s taking the time to guide me and give me insight and help me out so I feel like least I could do was pay his lunch. And so, when we got to leave, I had parked down, I guess, near where he was parked and I didn’t realize it. So, we leave the same time and he starts walking, this fucking guy starts walking to the nicest Tesla out there, this badass Tesla, next to him is my beaten ass Coke can parked right next to him and I’m slow walk just so he don’t see me get this truck.

I am paying this dude’s meal, and he did try to tell me no, he’s like, “Nah, don’t worry about it,” but I insisted.

So, it was stuff like that, trying to get people to go to lunch or hang out or just talk to people and get as much information as I can about the industry and about how to make it.

Adam: What did you think of smartphones when you first saw one?

Rick: It was amazing, in fact. I remember thinking this is incredible how much you can do from a phone and from a laptop. When I got arrested, I had a pager. And so, I just remember being so empowered like, damn, I could get my life on track from this room, whatever room I’m in as long as I have access to the internet and it was really cool.

Catching Up

Adam: So, Rick has a lot of tech to catch up on. Think of everything that’s changed since 1998 but he was obsessed.

Rick: A friend of mine got me this really old Linux computer and I didn’t know how to use it, it was an Ubuntu and he let me borrow it for a while, like a little old laptop and I would fall asleep till 3:00, 4:00 in the morning. I remember being so excited, I would stay up super late and, whether it was on the laptop or the phone, it was just 2:00, 3:00 in the morning because I could fucking look up whatever I want, I could learn whatever I want. It was a drug to me, it was pretty badass.

Adam: One thing Rick was looking up was how to fund his education and he found out about Pell Grants which is a federal student loan program.

Rick: It actually allowed me, it gave me enough with loans to not have to work a ton. So, it actually allowed me to code on the side without working a whole lot because they had the Pell Grant, there was different loans and grants but I had to go to school to get it. Well, the classes were really easy, it’s community college so it’s not super hard. So, I would knock the classes out real quick and then just do other stuff like coding or whatever and I used it to give myself time to code and to learn what I was learning. And damn if I didn’t need it because, man, I’m telling you, I didn’t know what an email was, I didn’t know anything. I was a kid when I went in. It was a lot of work, maybe I’m not a fast learner, I don’t know, but it took a long time. And again, though, it’s like a caveman. I literally was fucking figuring out what fire was and beating on this laptop till it made code.

How To Become a Developer

Adam: After enough lunches and meetups around Orlando, Rick did end up cracking the code on how to learn the skill, how to become a software developer.

Rick: I would look for ways that, first off, anything that will give you time. Even if it’s a job that’s maybe just a crap job but you’ll have a lot of free time, something that will allow you to study. Time is everything. You need some hours in the day especially if you’re going to catch up and try to actually be competitive. If you want to interview at top tier places, you’re going to have a lot of ground to make up because you’re competing with Stanford grads, you’re competing with University of Washington grads. So, you’re going to need a lot of time and you’re going to need a lot of commitment.

Adam: If you wanted to follow in Rick’s footsteps and become a top tier developer, here’s how you’d do it.

Rick: If I was starting over now from a disadvantaged background, if you can’t do the community college route like I was mentioning, I went to Eastern Florida State College and it allowed me time. And I know it’s not popular to just talk about grinding, the overwork culture is not popular. I get that, this is a different space. You want this shit? You got to grind. You’re going to have to do it on the weekends, you’re going to have to lock in. I’m sure someone’s going to be like, “Oh, no you don’t. I don’t have to. don’t put that pressure on them,” that’s fine. But to me, when you come from a background, especially if you’re a felon, but even if you’re not a felon, you don’t have a college that’s going to give you any kind of signal.

Everyone talks about the college debt but your local community college isn’t that expensive. And then, that way, maybe you could just cut your work down to 10, 20 hours and then spend the rest of time coding.

Adam: Once you found the time, the time for coding, you need a learning strategy.

Rick: You focus on fundamentals first. Data structures, control flow, that kind of thing and stick to that for a short period of time. Maybe a month, month and a half, just do that basic stuff. It’s not popular, people want to see things on their screen, they want to say they built a thing but you’ve got to get those fundamentals first and there’s so many free options, Coursera, freeCodeCamp. And then, once you get some fundamentals, then you can decide on the platform.

Adam: For Rick, smartphones were such an amazing discovery when he came out that he chose to focus on iOS.

Rick: And once you pick your platform, just focus and stick to it. If you’re building Ruby on Rails, do that every day but make sure you’re building it. Hands on the keyboard, watch a tutorial then do the tutorial again but change some things then try to recreate what you built in the tutorial while not looking, that kind of thing. Because that’s the main thing is getting your skills up.

Adam: So, while you’re doing all this, grinding out tutorials, you’re not done. Rick says there’s still another important part.

Rick: You also got to know somebody, you also have to talk to somebody, you have to know somebody. And so, the way you do that is just find a way to be around developers. Whether it’s meetups or online organizations, get involved and even donate maybe an hour or two if you can. You got to focus and build your relationships with intention, hang out, talk, be a part. We’ll go back to the cabbage field. I don’t care if they’re picking cabbage, go out in that cabbage field, pick cabbage with them and hang out. Just be around developers because those are the people that usually will help you get offer opportunities and you’ll know when they’re going to be hiring sometimes before the job ever even hits the job board.

Adam: Oh, that’s a great, great summary. People can climb from various socioeconomic backgrounds up but it’s a harrowing undertaking.

Rick: It is, it definitely is. And I understand why people push back on the don’t be hard on yourself, all the pressure, take a day off, it’s okay. And I get that, I get that but, when you’re coming from way behind everyone else in this rat race, you got a lot of catching up to do. I try to speak without bullshitting about what it takes because it does take a grind. And I know every boot camp out there, every coach and every content creator wants to create this narrative three months in a JavaScript framework and you’re getting paid and that’s just not how it is for most of us, most us are going to grind. It’s going to take a hardcore commitment, a lot of investment, you’re not going to see a return on it for a little while so that takes willpower. And maybe I’m just speaking for people I know, maybe it’s a small circle but I can tell you, from my own experiences, it takes a lot out of you. It takes a lot of grind and a lot of commitment.

Job Interviews

Adam: Part of that grind, once you have some skills is just grinding through some job interviews. You’re probably not going to get the first job you apply for. So, in the first couple of years, Rick got a couple interviews under his belt.

Rick: I bombed the interviews because I didn’t know what I thought I knew. I didn’t know shit and I thought I knew something and I found out I didn’t know anything. Did terrible in couple interviews I got. Well, one I didn’t do terrible but I think, also, at the time, I was nervous and there was a couple of questions that were asked that I knew. Later on, looking back, I’m like, “Ah, I knew what that was,” and I didn’t. For some reason, I think I was just nervous.

Adam: So, Rick is working his own three-stage plan. Find the time, get the skills, get the network. And when it came to networking, it turned out that one of Rick’s friends from before he was in prison was a super helpful connection.

Rick: He was one of my homeboys that, if you had problems, you would call her or whatever, that kind of thing so that actually played in my favor.

Adam: His friend’s wife was a dot net developer.

Rick: Well, he told her that, no, he really was always sticking up for somebody. And so, coming from him, I don’t know, maybe it made an impression on her and so then we hung out a bunch and she was like, “Yeah, I want to try to help you.” And so, she explained to the hiring manager and of course he’s asked what happened and I just told him I made some horrible choices and I can’t undo those, I can’t change it but I can tell you I’m not the same person. And if you give me a chance, I’ll show you.

Being Transparent

Adam: Did you ever think about just lying or covering it up or just, I don’t know. I would just try to not have it come up, that’d be my strategy.

Rick: I hear you and I’m very transparent. It’s a huge part of my life, it’s such a large part that it’s going to come up. At the time, it was half my life and all my life as an adult. So, it’s bound to come up at some point and I feel like I want to get ahead of it. If someone’s going to find out, I want me to tell them. I would rather be the one to tell them. And if you’re going to refer me, Adam, I wouldn’t want later on the hiring manager to come back and be like, “Damn, Adam, you could have told me this guy’s went to prison.” I like people knowing they can trust me and so there is that. If you’re going to refer me, I’m going to make sure you know I come with some baggage and this is that baggage.

Adam: So, the hiring manager wants to hire him but, after hearing about his past, he decides he should check with the whole team.

Rick: So, he asked everyone in the office because it was in person. He had to talk to them to make sure they were all cool with it. There’s not many groups of people that you’re going to find where everybody’s okay with someone coming on premises that’s killed someone and everybody was, they’re like, “Yeah, it’s fine.” And here I am out here with normal people who somehow find it in them to be that open-minded and understanding and empathetic, I guess, been pretty bad ass when I’ve met people like that.

Twitter Time

Adam: So, it took almost three years, two years and eight months but now Rick is a professional developer, he’s being paid to write code. The next step, of course, is to get on social media.

Rick: I tweeted that I got a job as a software engineer, I mentioned my background and I had a ton of people reach out. And a lot of people started asking me, “Hey, I have a felony or I did time or whatever, would you help me?” So, I got the small group together, got them all in a text group and so we’d text and all of us would chat on just this little text group.

Adam: So, Rick names this group Underdog Devs and, along with his new dev job, he becomes a leader and a coach for this group. He’s this model that other people can aspire to.

Rick: I feel vindicated on having been so open so early even with my Twitter or whatever I do because a lot of people have told me, “Man, it helped. That fucking helped me a lot. Seeing you be so transparent, seeing you win.” And that wasn’t purposeful, I’m going to be honest, I didn’t do that intentionally. “I’m going to help everyone else feel brave,” I wasn’t trying to make anybody feel brave but it did that.

Ryan’s Story

Adam: Well, Rick’s inspiring people and helping them via text and building up this mentoring process. His friend, Ryan, his co-teacher from prison, the prison Python class gets out of prison.

Rick: And he did the same thing I did because I’d given him my advice on what I think we should be doing. So, he joins the community college in Eastern Florida State College, gets the same degree I did and he’s doing good, he’s got a lot of grit, he just does the interview well. He’s terrible at interviews. Dude’s super smart, super smart but you wouldn’t know it in the interview. He just doesn’t the interview well and his whole background is all construction. At first, he was doing a lot of power lifting, he was doing a lot of other stuff and we had that come to Jesus, as they say, talk where you’re just real with each other.

And I was like, “Dude, you got to fucking give some of this shit up. It’s not going to work, man. You’re going to squander, you’re not going to get hired. You got to get your skills better than what people suspect because we don’t have strong signals, we’re not sending strong signals. I don’t have a Stanford degree and we have felonies, your skills got to compensate for that and so you got to give up and you got to lock in.”

Adam: So, Ryan gave up on power lifting and he committed to grinding out his programming skills. And by this time, Underdog Devs had become something bigger. It had moved to Slack, it had suggested classes and it had a collection of mentors from the industry. Mentors are part of Rick’s original formula of time plus skills plus network. You need to hang out with developers to become a developer and your mentors are there to help that process happen.

Rick: So, we got him in Underdog Devs, he was grinding. And eventually, he showed commitment and we got him in Project Underdog.

Adam: Project Underdog is a special program in Underdog Devs where you get some financial assistance, we’ll get to that shortly.

Rick: So, found out he got hired and, I’m not going to lie, I teared up a little bit. But I’m listening to him, he called me, we put him on speakerphone, I’m like, “So, what’s up?” He just starts grunting on the phone, he’s like, “Dude, they gave me an offer, uuuuuuuugh,” and, dude, I was laughing so hard. I’m like, “What the fuck are you doing?” I’m like, “Is that a grunt? Are you grunting at me, dude?” And he’s grunting on the other side of the phone, it was funny but that’s why you do it. That’s why, to me, Underdog Devs flourishes without a dime going into operating costs, moments like that.

Adam: I think grunting is the power lifting cry.

Rick: I didn’t think about that but you’re right, that’s how he should communicate. That is power lifting language, I think. I don’t know, I don’t power lift but, yeah, it’s true.

Ricks’s Friends

Adam: So, Underdog Devs grows larger, they get some help from Udacity on course credits, they become a registered nonprofit, Rick gets advice from Big Nerd Ranch, Jessica McKellar whose company was sold to Dropbox joins and starts helping out. And meanwhile, people from Rick’s childhood, they start noticing how successful he’s become.

Rick: Everyone I was close with growing up, my circle. Clearly, I’ve made a lot of other friends since then and my friend groups are varied now but, the group I grew up around, they’re all doing construction stuff. So, yeah, there’s quite a few that were like, “What the fuck?” They watched me go away, some of them came and visited and then they watched me come back and now I’m in an industry that they have never been around. And I’m like, “I tried to tell you all. Hey, let me help you out.” In fact that’s how Underdog Dev started was people reaching out like, “Hey, how’d you do that? How did you do that?” How did you go from prison to programming as a profession and me saying I could try to help you if you want.

UnderDog Devs and Project Underdog

Adam: So, the scope of Underdog Devs expanded. It went from helping felons to helping all kinds of people from lower socioeconomic backgrounds like Juan, a construction worker who’s in the program right now and trying to become a professional software developer and Rick is always looking for more mentors.

Rick: Okay, so if you want to help out, we got a couple ways. The most general mentorship is one hour, biweekly and this is more general. It’s up to you, it’s your agenda, you guide them and we would love help with that. You’re helping people that are really good people, they’re good people that made poor choices and they’ve been trying to get their life on track and they just don’t have the network because they’re from different environments. And then we have Project Underdog, which is special, which Jessica McKellar helped start. And Project Underdog is where we take people like Juan, I’ve seen him, he’s got grit, he’s smart, his circumstances just don’t allow. He’s got to work construction all day, he’s got to help his family and he’s probably in … The statistics lay this out for us in our country, when you’re born into a lower socioeconomic background, when you’re born into those spaces, you’re going to probably die in those spaces, it’s hard to break out.

Well, coding levels the playing field. It allows for, if you got the skill, you can do it but you also have to have the time. So, with Project Underdog, they get the time because we find the people who are grinding without it. He would come home from construction and work and code and jump on meetings. And so, we select those that have shown a lot of grit and consistency and bring them in and, for that, we need mentors who are really skilled for that. And every mentee gets five mentors. And so, Monday to Friday, they pair program with a different mentor each day from these problem set that Jessica’s built. It’s not necessarily LeetCode-ish, we’re not asking them to worry about time and space complexity but we are asking them to solve problems and to pair programming guide the mentee.

So, for that, that’s an hour a week, it’s the heartbeat of Underdog Devs and you’ll see stories that will bring you to tears. If you’ve got any emotion at all, it’s the most amazing stories you’ve ever seen. There’s a reason that we’ve been doing this, we’re going on three years now, there’s a reason we do this and I don’t get a dollar from it. Every bit we have, all our stuff goes to the stipends because I feel like that’s how we can expand access and it’s rewarding itself, it’s rewarding in itself. I don’t need a dollar, Jessica’s rich, she don’t fucking need no money. And so, you’ll see, once you get involved and you do it and you see people’s life change, I’ve heard it over and over and over, I can’t express this enough, people telling me, “Whoa, this has been life changing. This is pretty badass,” just saying how meaningful it is to them.

Life’s Not Fair

Adam: That’s awesome. You mentioned it there, I was just thinking about it. Do you think we live in a fair world? Do you think that people from these lower income areas have the same crack at things that everybody else does?

Rick: No way, no way. You can’t, you can’t. I’m not saying that everything’s completely unfair, we have a lot of opportunity in the United States, clearly. I’ve done all right and I had a lot of odds against me. But if 95% of the people born into lower socioeconomic standing die in that same space and you don’t rise above it, there’s something there, you can’t tell me that’s random. You could blame culture, you could blame system, there’s lots of elements. I’m not a trained sociologist so I’m not going to say that I know for sure but I am going to say it’s clear that there’s a disadvantage to being born into certain spaces. My own journey gives hints at that.

In fact, talking to my daughter, she’s into coding, she’s making all A’s, discussing Deep Work, the book, with her, the contrast in how I was raised, that by itself, that by itself just sits with me. Fuck, we’re discussing the value of concentration in Cal Newport’s work on the study of concentration and focus. And on the other hand, when I was her age, I was probably trying to talk my dad into letting us put a keg. And it’s just an example, there’s lots of other stuff. Just environments that are toxic, one parent is discussing college opportunities, the other parent is screaming that they’re going to blow their head off and leave because something happened. It’s different environments, definitely not fair. You automatically just assume there’s a ton of economic mobility but there’s not, it’s not what you think.

There’s not a level playing field completely. There are opportunities though and that’s the main thing our group does is try to make sure that people have opportunities. If they do have grit and they have tenacity, we want to be there so that they’re not just washed out because of the circumstances. And I’m not saying that I’m systemically held back, there are people that are systemically held back, I don’t think I’m one of them but, where class is concerned, there’s a lot there that affects people that you don’t look at. There’s a lot of things holding people back from certain spaces and certain backgrounds that aren’t necessarily noticeable from the outside.


Adam: That was the show!

A big thank you to Rick for sharing his story. Go to to check out the program, find him on Twitter and also in the show notes.

And if you like the show, share it with somebody so they can learn about it as well or just spam it in the off topic channel at your worker in some Discord server, I don’t know.

And if you’re a super fan, support me on Patreon to get access to more episodes and just encourage me to keep making them.

And until next time, thank you so much for listening.

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I make CoRecursive because I love it when someone shares the details behind some project, some bug, or some incident with me.

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