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Episode 102 January 30, 2018 | 27min

Venturing Into America’s Prison Problem: A Conversation with Chris Redlitz

Chris Redlitz talks about curbing mass incarceration with venture capital.

Show Notes

This week Paul Ford and Rich Ziade sit down with Chris Redlitz to talk about his newest venture, The Last Mile (TLM) — a nonprofit building technology incubators and coding schools within prisons. We talk about access to information, the stigma around hiring incarcerated individuals, and the tangible steps we can take to curb mass incarceration and reduce the recidivism rate in America. Rich also reveals his subconscious love of tight polyester pants!

[Intro music] 00:16 Rich Ziade Welcome to Track Changes, the official podcast of Postlight Studios. We are a digital product studio based in New York City. We design and build amazing platforms, applications, mobile — all sorts of technology product. And sitting across from me is my co-founder, Paul Ford.

Paul Ford So that’s Rich Ziade, I’m Paul Ford, and we’re gonna talk about something serious.

RZ Yes. I’ll get some jabs in but it’s pretty serious.

PF Yeah, prison reform is a pretty deep issue in America right now.

RZ Nasty puzzle.

PF Yeah and so the person we’re gonna talk to is someone who is both from our world, a technology leader [mm hmm] and venture capitalist, Chris Redlitz is his name and he –

RZ He pivoted.

PF He pivoted –

RZ But this is a heck of a pivot.

PF Yeah, pivoted to San Quentin. So, let’s talk to him.

RZ So Chris, welcome.

Chris Redlitz Thank you. Thanks for having me.

RZ Sure. Um we’ve got a lot to cover but I think it helps to give context and, in this case, context is where you’re coming from, what you’ve done before this organization came together.

CR Sure, I’ve been in Silicon Valley for about 20 years, working in a variety of start-ups. Founding startups, investing in start-ups as an angel investor, and then about eight years forming a venture capital firm. We started out really with a fairly domain focus around digital media, mobile commerce, um and then software services for enterprise um companies. We’re — you know — we sold a company to Snap, so we’re an investor in Snap. That’s probably the company that people would recognize most. But we’re also investors in a company called Wish which is one of the top ecommerce apps, you know, on the web.

RZ We are fascinated with Wish [CR chuckles].

PF I would say, in particular, Rich is fascinated with Wish.

RZ I mean the fact that I can get a lawnmower for three dollars is [CR laughs] something. I browse Wish with no intention of buying which I think is part of their story, so –

2:30 PF When they came to you, what was attractive about that pitch?

CR Well, actually, Peter, is the CEO, ran uh the technology team in Korea for Google. And –

RZ Oh interesting.

CR — his original premise was around [sucks teeth] advertising and building a — basically an alternative to Google AdWords and Google AdSense. Um but what happened was over time he took that taxonomy and that — that approach to advertising and pivoted into ecommerce. So the same sort of idea of predictive analytics and um really being able to target is what is the backbone of Wish.

RZ I gotta tell ya: that’s disturbing to hear because as Wish has gotten to know me, it’s been suggesting really, really tight polyester pants [CR laughs] and I don’t know what to make of it.

PF Chris, when somebody comes to you with a pivot like that, when somebody shows up and says, “Yeah, ya know, we were gonna take on all of Google but [RZ chuckles] but instead we’re gonna take this recommendation engine and, ya know, given the way that global commerce is going, suggest a lot of polyester pants and cheap electronics. What –

CR Yeah.

We’ve seen some of the best companies come out of pivots or side projects.

PF — was that good news? Was that bad news? How — what’s that like when you’re on the other side? And what was the right way to tell a VC this big news?

CR We’ve seen some of the best companies come out of pivots or, ya know, side projects. So, frankly if the initial tact or initial target is not working, you know, looking at alternatives uh we don’t necessarily discourage that. I mean we’re, as investors, we act as advisors and sounding but we’re certainly not gonna tell, you know, founders and CEOs what to do and how to operate, so [RZ hmm] he did very stealthily. I mean the company raised some money, started Wishlist on Facebook and it really gain momentum and caught people by surprise. I think a lot of people don’t even know about Wish today even though it’s uh, you know, generating billions in revenue and –

RZ Yeah, it’s a monster.

CR — it’s a monster and a lot of people don’t even realize it.

RZ Yeah, it’s a fascinating company. Ok so, obviously a lot of success as an entrepreneur and as a VC. Tell us about what steered you towards really doing something well outside of the VC and investment world.

CR You know I’d never really had any kinda social cause and I wasn’t particularly, deeply involved in charitable organizations, to be honest, and um in 2010, you know, I live in San Francisco, I obviously work in the Valley, and I was invited by a friend into San Quentin which is, people don’t know, it’s about 30 minutes north of city. So it’s pretty close and she asked me to come in and talk to a group of men about entrepreneurship and business and because they said there’s this desire inside prison for people to understand business and they just don’t have any outlet or resource. And my initial reaction to her was, “No, I’m not interested.” But she persisted and I agreed to do one evening, go in and uh speak to this group, and she said, “Look, come in prison, 30 minutes, you’re out. You’re done your thing and, you know, I’ll have fulfilled my promise to the men.” So I went in um, you know, and going into San Quentin is pretty daunting. It’s the oldest prison in California, it’s got a lot of history, it has death row. And so you’re walking in there and I did it at night, you know, I’d never been in a prison before so it was uh obviously I was pretty petrified, to be honest, and I walk in this and there’s about 60 guys packed in this room.

6:13 RZ Wow.

CR And I thought, “Uh, you know, I don’t think they’re gonna understand anything I’m gonna talk about but I’m gonna do it and leave.” Um and what happened was I started talking and almost immediately hands went in the air and literally the 30 minutes turned into three hours.

RZ Wow.

CR But I was, literally, left prison, my head was spinning, and I was just like, “I think there’s something here.” And I walked in the house and I said, “Beverly,” who’s been my business partner and she’s been involved in some of things from day one for startups and I said, “You know, Beverly, you can’t believe what I saw: I think we can start a technology incubator inside San Quentin.”

PF So the same kind of Spidey sense that goes off when you see an interesting and attractive investment sounds like it went off when you went to San Quentin.

CR Well, you know, I talk a lot about the look that you see in a founder’s eyes. Sometimes, even with Peter with which — it’s like right away that ‘it’ factor. And I saw that in some of these guys in this classroom. They had — just had this look. They had this passion and thirst to create something after they served their time, to be successful. You could just see it and, you know, I thought everybody in San Quentin was Charles Manson, right? I had no idea and I just started to see this human element of people that I didn’t expect and this real passion and desire and it just hit me. And um literally that — that favour to a friend has changed my life and this whole thing has become really a life mission for me.

PF So you go home, you tell your wife, you say, “This is it. We’re going in a new path. We’re gonna do -” What did she say right away?

7:58 CR She said, “No effin way am I goin’ to prison.” [PF and RZ laugh] ironically today, Beverly is the executive director of our non-profit.

PF This is how marriages work, you know? [All laugh] how did you set up this organization? Where did you start?

CR Well, um, I, again, went back to the woman that originally uh suggested and I said, “You know, this is my idea.” She said, “You know you need to talk to prison administration if you’re really serious about this. You know, they’re really careful about programs they let in and blah blah blah.” So I went to the warden, kinda pitched the idea, I guess I would say they reluctantly gave us permission to do a evening program with a very small group. So uh you know and I also didn’t know any of the inmates, so I really relied on them. “Can you help select some of these people who will really be sort of our beta test for this program?” And they did, we started out with seven guys, um, and Beverly and I went in to San Quentin two nights a week for one year and we basically kind of made up the program and it was kind of directed around what we were already doing with our investment practice and our incubator where we were bringing up to speed that had been incarcerated for a long time about technology even though we had no connectivity. We had them come up with a passion idea that they turned into a business plan, they built a presentation, and then we had our first demo day in San Quentin that I brought in outside investors and just like you would see a demo day in Silicon Valley.

PF What were the products?

CR Kenyatta Leal who was now on our board of directors, his idea was called Couch Potato where, you know, he’s a big football fan. It was basically an app that you could build where you could basically call plays real time and get points for getting the right plays. Uh we had another one, it was a mobile haircut idea, and the twist was converting school buses into mobile haircuts and having the ability to send your playlist prior to getting your haircut and actually having your own playlist as you’re getting your haircut inside.

RZ That’s cool.

PF These sound completely viable. I mean [RZ yeah!]. I mean they’re no more ridiculous than a subscription box of deodorant sent to your house every month. I mean –

RZ Or polyester pants.

PF Yeah.

CR Yeah, exactly [chuckles]. No and, as a matter of fact, uh James Huston who was in our first class. His idea was teen tech cut up to actually create after school programs uh primarily around entrepreneurship and technology uh and he had come from Richmond in the East Bay which is one of the most — it’s one of the roughest neighbourhoods really in the State. Um he’s now a — works for the City of Richmond and he’s actually doing exactly what he had pitched on demo day. So, you know, some of these things do come into fruition. But the ideas that they came up with were pretty amazing and even more so: how they presented. Um I had, you know, VC friends come up to me afterwards and say, “Chris, these were great presentations and some of the best I’ve ever seen.”

11:04 RZ Wow.

CR Because these guys they practiced, they honed, and I what I say a lot is: “Take this presentation from your head to your heart.” And when they were presenting the emotion, every single one got a standing ovation. Just because they were so awesome. And now I said, Kenyatta Leal who was in our first, he’s on our board of directors, he was serving a life sentence when I met him as a result of the three strikes reform. He was released, now he’s on his four year anniversary and he works for a technology company here in San Francisco. You know someone like that has just become a beacon of hope for those inside.

PF What was hard for them? Like, obviously they don’t have access to the most recent technology. So that’s one big gap. What are the other challenges that these people are facing when they’re going through this program?

CR The first thing that we recognized was that many of them just lacked hope. They lived in a box and they thought in a box. They didn’t have big dreams and aspirations and part of what we did originally was break out of that, you know, think about something that, regardless of what the — you think the obstacles are, forget about how much money it would cost, what would you do and how would you do it? And so our first really premise was to instill hope and confidence and that they could dream big. We did the entrepreneurship for four years, then we launched our coding school four years ago. So now we actually have [sucks teeth] — guys are learning to be software engineers, which is obviously a big leap. And we also established a technology development shop inside San Quentin. So we actually can work on projects for outside companies now and the guys get paid a wage that’s the highest ever wage paid in prison. So it’s come a long way from this idea of just instilling hope. Now we have teaching practical skills and we have guys getting out, getting hired as software engineers. We just had three guys hired within the last month in the Valley as uh Javascript coders.

He was serving a life sentence when I met him as a result of the three strikes reform. He was released, now he’s on his four year anniversary and he works for a technology company here in San Francisco. Someone like that has just become a beacon of hope for those inside.

RZ That’s amazing. I just — I’m trying to connect the dots here: I mean, obviously, I have a stereotypical view of prison.

CR Yeah, sure.

RZ I just imagine, you know, the courtyard –

13:24 PF Well there’s what we see in movies and TV.

RZ Yeah and some of them are doing like weightlifting. It’s just that’s the scene that is drawn over and over again. What’s astonishing to me is I can’t make that leap. I can’t make the leap from the courtyard to what you’re describing and, more than anything, I guess in my mind, I just can’t find the motivation, not even just demos, like just standing in front of everybody and doing it. Like were you shocked by the interest level?

CR Yeah I mean, again, I saw that nugget of real, genuine interest. So we drew on that. And, look, I approached this as a start up. I approached it the same way that I would approach a business. So I walked in and said, “Look, we’re gonna treat this like we would treat any business. And that means that um it’s a zero tolerance: if you screw up, you’re out.”

RZ Hmm.

CR But I’m gonna — I’m gonna provide opportunities. And when I first said, you know, “When you get out of this program, you’re gonna get a job in Silicon Valley.” They looked at me like I was crazy.

RZ Sure.

CR Like, you know, that can’t true. So part of it for me and for Beverly was to get their trust to have them believe –

RZ Amazing.

PF What do prisoners make of stats? I’ve never thought about that. I mean like you don’t have access to metrics in jail.

The first thing that we recognized was that many of [the students] just lacked hope. They lived in a box and they thought in a box. …And so our first premise was to instill hope and confidence, so that they could dream big.

CR Mm hmm, yup.

PF Was that a revelation? Was that just sort of interesting?

CR It was huge. Again, it’s, “In prison I don’t have a voice. Right? I can’t vote. No one cares what I think. You know I have access to TV and newspaper but I don’t have an outward access to express my opinion. And all of a sudden you do. And you get that response. It’s transformational.”

RZ Ok so you’re seeing success, it’s inspiring, tell me about the institutions.

CR Sure.

RZ And their reactions. I mean, all the way up the chain from the prison to the prison system or the bureaucracy around prisons and onward, upward.

15:28 CR Yeah. Well it really starts in the yard. You mentioned the yard before. I mean it truly is like you see on TV. You know. And in San Quentin it’s kinda unique because um I can walk you know in the yard, you know, by myself and, you know, I have clearance to walk around the prison. Uh it’s very unique. And the yard is, like any other yard, it’s, you know, segregated, and there’s basketball going on and everybody doing their athletics and whatnot. It’s pretty typical as you see. Um but uh when we first started the program, we started also an author series where I would bring a business book in and I would invite the author in after the guys read the book. So the first book we had was Guy Kawasaki’s Enchantment. So Guy, you know, [sucks teeth] he agreed to do it. The unique thing was these guys were walking around the yard with this little red book and it became [RZ chuckles] kinda this mystery like: who are these guys? And what is this book? And that kinda started it. Um now we have guys walking around with Javascript books in the yard and they’re talking about coding and it’s become kind of a joke. So the mindset started in the yard, the prison administration was looking at this, and one day Matt Kate who, at the time was the secretary of prisons in California, runs all the prisons, he was at San Quentin and I met him and he became a big champion. And I think that, for us, was sort of the pivotal point where we actually got the support from Matt, Governor Brown found out about it, he supported it, and then they really got behind it. I was resistant to take any money or any support from the state originally but now we’ve created a partnership where they’re underwriting a lot of what we’re doing. But it really sort of started in the yard, went to the warden, and then, you know, went to Sacramento, and now, today, we have conversations with many states about expansion and, you know, we’re looking at, in 2018, expanding what we’re doing it. And, for a lack of a better term, sort of franchising this idea and our curriculum to, you know, anyone who wants to fund it.

RZ How can people help?

CR You know the big thing is, for us, has been the community of companies from volunteers. We have about 90 volunteers just for San Quentin. Every other Wednesday we do a trip where we bring in about 15 software engineers, coming from all technology companies here in the Valley, and they sit with our guys and work with them for several hours. So the volunteer idea and the participation has allowed us as a still a very small core team to grow. So volunteering is one. Second is the receptiveness for companies, whether it’s a small start up or a larger company, to give these guys a chance and we’re not asking for a gift. They have to earn this job. But being open and receptive to hiring formerly incarcerated. And what we found is that these men and women don’t make good employees, they make great employees. And some of the CEOs have hired them and saying, you know, “These are some of the most passionate, dedicated employees I’ve ever had.” You know and obviously as we expand financial support, most of it has come from the state. You know as we expand obviously that’s always a challenge. But the goal for us, as I mentioned, with the dev shop, it’s under our non-profit. So all the proceeds that would generate through the dev shop get recycled. So ultimately we want to be a self-sustaining non-profit based on the business that we generate. So if there’s companies out there that need websites or web apps um we can do those jobs as well. We can do them quickly, competitively. So you’re actually getting a good product but also, you know, providing a social benefit as well.

19:34 RZ Is it possible or have you thought about how organizations or people can help once ex-prisoners are out? There are people that get out who obviously don’t get wind of the program or, for whatever reason, aren’t able to hop on, but they’re out in the world and –

CR Yup.

RZ — their facing the world and an opportunity like or at least a path to that opportunity would be huge.

CR Yeah I mean we’re partnering with other reentry organizations because we can’t solve all problems at one time. But we’re really focused on inside education and preparation when they hit the gate. But we do, obviously, placement for graduates but we’re also partnering with other organizations that help with reentry: transitional housing, there are support groups that provide clothing and those type of things. Just having a manual labour job or a, you know, minimum wage job is a step in the right direction. So –

RZ Mm hmm.

CR — you know, being receptive to hiring formerly incarcerated. But also not lowering your standard. You know, having the same expectation you would from any other employee. You know, the accountability has to be there. It just — sort of dovetailing on your previous question where what are some of the implications: we’ve had, in every institution, wardens tell us that incidence levels are down because people are thinking about how they need to operate and, you know, if they’re sort of on the edge of doing something that they shouldn’t be doing and they realize that if they do that, they’ll never be accepted in what we’re doing. Then they’re sorta making a decision at that point. So it’s really helped the culture inside the prison as well which, again, that was a — sort of an ancillary benefit that we never even considered.

RZ Right.

PF So I shouldn’t ask this question, it’s not a fair question, but: how do we fix the prison system in America?

RZ Poof! You’ve got 60 seconds [all chuckle].

PF I just think you might have an opinion [RZ and CR laugh].

CR Well, obviously, we’re way over incarcerated and, you know, the number’s been thrown around a lot. But, you know, we have 25 percent of the prison population and we have five percent of the overall world’s population. So, we’re by far the most overly incarcerated population in the world. Obviously, we’re changing drug laws which are gonna hopefully have impact on the amount of people they’d get incarcerated. We’re looking at many prosecutors and one of the most well-known, Adam Foss, who did a phenomenal TED Talk, talks about alternative sentencing where instead of throwing, especially juveniles, in prison, let’s find maybe a health remedy. And plus the extended length of sentences is really being addressed and that’s been addressed in California with several initiatives. One started with Prop 36 which, as I mentioned before, it really evaluated and restructured the three strikes law. And three strikes was basically saying that if you had a third strike, that you got a life sentence, minimum 25 to life. And you could’ve had a very minor infraction literally stealing a loaf of bread, which was a documented case, given 25 to life. That’s changed. You know, that’s been repealed in a sense. Um, Prop 47 was one recently which looked at how do judges uh [sucks teeth] they have sort of flexibility in assigning misdemeanour felony and then uh Prop 57 recently looked at juveniles who were incarcerated and given life sentences and readdressing that. So, you know, I think it’s looking at what we define as a crime but also the extent of sentences and really what we’re also doing is creating a sort of reward system in a sense where if you do the time and you do it right, that should be acknowledged. So when a lifer goes in front of the board, they are looking for those that have done the work and being receptive to releasing. So about half the guys in our program were lifers originally and now they’re out doing phenomenally well. So I know it’s a long answer to your question, it’s probably over 60 seconds [RZ chuckles] but I think it’s at the start. You know, looking at how we’re defining what’s a crime but also evaluating um people inside and determining when they’re ready and what effort they’re putting forth to be ready.

24:17 PF Entirely sensible answer.

RZ You deserve the extra time [CR chuckles].

PF So people want to get in touch and help, where do they go? What do they do?

CR thelastmile.org, we have a Twitter feed: @tlm. You can send an email to us: [email protected] or there’s a tab on the website um that you can fill out a form if you want to donate or donate your time or your money or whatever. Um or if you just, you know, wanna reach out and say, you know, “I have some ideas.” We’ll respond to every email. And we may not be in your state or city today but the goal is to be out there. If you can’t volunteer today [music fades in], maybe you can in the future.

PF Well it’s great work and thank you very much for coming on.

RZ Yeah this is — it’s inspiring to hear the story and the work you guys are doing.

CR Well I appreciate you guys having the interest and, you know, thanks for giving me some time. Appreciate it.

PF Well, look, that is some real stuff!

25:16 RZ Yes, amazing.

PF That is, you know –

RZ Inspiring.

PF — he’s a leader and he’s talking to us, you know making sure that the message gets out but that’s some tough stuff to deal with.

RZ Without a doubt.

PF Yeah I mean you’re talking about people with life sentences who are trying to get back into society. That is some — that’s a deep cut.

RZ It is and, you know, not a lot of positivity and there’s not a lot of good turns in the plot these days and it’s great hear a story like this.

PF I think also it’s just right now we’re in this zone where technology is under necessary interrogation. Like, what is the role of the Facebook in our society?

RZ Yup.

PF It’s good to see just like there is that transformative power to learning how the machine works –

RZ Yeah.

PF — and getting into the economy.

RZ Right.

PF And getting from one station in your life to another. And this an extremely dramatic version of that.

RZ Yeah this is where technology is doing good.

PF That’s right and it’s just like and it’s empowering. I mean you just like, that part, that fundamental empowerment is so important to remember. And that’s it! Thank you for listening to Track Changes.

RZ Have a great week!

PF Bye [music ramps up to end].