#29 Rick Wolter: from prison to software developer, building Underdog Devs community to help the formerly incarcerated
iOS software developer and founder of Underdog Devs, US based community of software engineers helping formerly incarcerated and socioeconomically disadvantaged people make it into tech
We are Pol Fañanás and Gerard García, two friends passionate about tech, startups, and VC, getting views from exceptional people building the future and sharing it for free with those who lack access. Thanks for reading!
Rick Wolter is an iOS software developer and the founder of Underdog Devs, a US based community of software engineers supporting formerly incarcerated and socioeconomically disadvantaged aspiring developers who want to get into tech and change their lives for the better.
Underdog Devs provides high quality education opportunities that lend jobs to those who need it most, via key factors like mentoring, pair programming, network, guidance to get hired and even taking care of the living expenses (from food to housing) of the mentees that can’t balance education and work because significant lack of basic resources. Everything, for free.
But that’s not all. Rick has an unusual background since he himself has gone through something similar to what his students experienced. Rick had a rough upbringing and after a mix of horrible decisions and bad circumstances, he was sentenced to 21 years in prison at 18 years old, after getting involved in a fight while protecting a friend who was getting jumped, that ended up with a man dying at the hospital and with Rick charged with 2nd degree murder. In prison Rick discovered he liked programming, pursued this passion, eventually made it into tech and started helping others with similar backgrounds change their lives and have some hope.
Summary
👤 Story: challenging background, trouble, prison, developer, helping others
🥇 Win: helping formerly incarcerated students make it into tech
🚫 Fail and lesson: struggling to get resources to help the bottom of the bottom
🚀 Great founder: hardcore passion, deep meaning, take action
💸 Great investor: understanding real underlying value, have strong conviction
📈 Markets: mobile development, QA
🦄 3 startups: Pilot, Udacity, Big Nerd Ranch, Checkr, Dropbox
👍 3 investors: John Carmack, Alex Marcy, Wil Reynolds
📖 3 books: "Deepwork: Rules for Focused Success in a Distracted World”, “Atomic Habits”, “A Confederacy of Dunces”, “The Signal and the Noise: Why so Many Predictions Fail - but Some Don’t”, “How Not to Be Wrong: The Power of Mathematical Thinking”
What is your story?
I’m from Orlando (Florida, US), I grew up in a dysfunctional middle-lower class environment, moved around a lot, got into some trouble and by 18 I already was in and out of jail a lot.
At 18 years old I was involved in a street fight that ended with me stabbing a man who later died at the hospital. At the time I felt like I was protecting my friend who was getting jumped but it was an overreaction and I was out of control.
I was charged with 2nd degree murder and sentenced to 21 years in prison. I had many issues, I made terrible choices and going to prison I think was the right thing for me at that time.
After that, my brother made sure I understood the importance of education and helped me get whatever educational resources I needed, which was really important for me especially since in the Florida Prison System at that time we didn’t have many educational options. Thanks to this and some other friends and family who shared books with me, I was able to obtain something resembling an education.
Then, after reading about the The Last Mile program in San Quentin State Prison doing stuff like teaching incarcerated people to code, I got inspired and started to learn programming on my own. At that time we really didn’t have much access to computers with one exception, a drug treatment center within prison which had some computers. I had a thumb drive with Python and some YouTube videos on programming snuck in and installed on those computers. With those resources I took to learning to program until the warden found out and transferred me because of it.
But it was not only about me, I really liked teaching in prison to other inmates and at the same time got help from my colleagues. I remember sharing articles about programming while learning together with people from all walks of life. Weeks before, you could see them with their gangs not doing anything good and suddenly you are learning all together in an exciting environment, sharing job demand, average salary - nurturing that spark.
Eventually I got out and to be honest still struggled quite a bit. But I had the blessing of having the gigantic support of my best friend, my wife. We grew up together, she knew me before all this prison stuff happened, she was there through all the shit despite my felony and has been there ever since.
After getting out, It took 3 years for me to get hired. I focused on getting a college degree and acquiring valuable programming skills while building a network, trying to overcome the setback that my poor decision-making had caused.
Following all of this, I thought damn it could be really interesting to help the people coming behind me who are also struggling because their disadvantaged profile, so they have a high quality network to support them. Consequently I founded Underdog Devs and started helping other formerly incarcerated people become developers, providing mentorship, high quality education, an opportunity to better jobs and ultimately an improved life quality.
What is the biggest win in your life?
I think the individual success stories of our students is that win. Seeing that crazy life change that probably won’t happen if we weren’t there to help, is incredible.
A special one that comes to my mind is Ryan. Ryan was with me in prison for over 6 years, we sneaked in together that Python thumb drive to put it on the computers and learn, and he listened to all recommendations and acted accordingly. Got out of prison, worked in construction while continuing learning at the same time, changed from web development to android development when I mentioned that web dev was getting saturated as a result of bootcamps activity (again listening to advice and acting accordingly) and eventually he got a job as software developer.
It was fun because he is this “alpha male / formerly incarcerated / construction worker” type of man, and my wife and I used to wonder if he would get emotional when he finally got a new job. Then it happened, I got a call and it was just him grunting on the phone for a while and then saying: “Dude, they made me an offer”.
What is the biggest failure and lesson?
I guess there are lots of things I could mention here, but I’d like to mention the difficulties we have experienced with funding.
When you are building high quality education for free while getting 0$ money from it and allocating 100% of resources to the mentees you are trying to help, and at the same time you see money flowing in other directions to organizations that you know are not really as impactful as they claim, it is a bit disheartening.
Sometimes it can be tough to come from the real true bottom and work on helping people overcome the same situation, in a world that not always care, while you see projects or people with more privileged backgrounds acting as if it was the same case when it really isn’t.
Maybe I underestimated how much politics, relationships or time play a role in obtaining the resources to get more people out of the gutter.
What is your description of a great founder?
Passion. I know it is a cliche but there is truth to it. I don’t see how are you going to do it if you lack hardcore passion that provides you the motivation and meaning to take the life changing actions you need to be a good entrepreneur. For instance in the case of Underdog Devs, I remember that in addition to working, studying and helping others, I used to do 50-100 personalized cold reach outs every weekend just to see how we could improve the help we provide.
What is your description of a great investor?
It’s not like I have a lot of experience with investors and maybe it sounds too simplistic, but based on what I’ve seen in the software development world I believe the two major factors for a good investor should be to truly understand the underlying value of the business and to have real faith in whatever it is they are getting into.
Regarding understanding the real value, I don’t really like when investors let politics and other type of subjective bias cloud their analysis. However I think this happens way more than it seems, more than what it is shared transparently.
And about having conviction, when I think about an scenario like looking for supporters that can help us literally change the life of people in need with Underdog Devs, it’s just too difficult to imagine a great investor that hasn’t a huge believe in the team and what we are trying to accomplish. Similar to the passion factor of the entrepreneur, it can be a very hard and challenging adventure so even though there is asymmetric information and you’ll always take risks, a moment in time comes where you need to have solid faith if you want to win.
What markets are you most interested in?
Talking from the point of view of a software developer / software engineer, I think there are a lot of interesting opportunities in mobile development. There are so many choices in web tooling that it is paralyzing, but mobile is a pretty clear cut and a nice target for new devs that want to get skilled quickly and play a role in the space.
I also like QA (Quality Assurance). I’m aware it is not super popular nor super highly paid, but again I think it is a pretty interesting and differential angle to get into tech. In all honesty never helped someone become a QA expert like I did with mobile profiles, but it feels somewhat similar to what I saw with people specializing in Android. Not a lot of devs focused on it, you can learn pretty fast, shape your resume in a distinctive manner and get hired pretty quickly.
3 startups you like and why?
I am going to be very biased but I will mention:
Pilot. Fintech startup whose Founder and CTO Jessica McKellar helped us make Underdog Devs what it is today, hired developers from the initiative and it is lead by incredible people who are very mission driven and extremely supportive.
Udacity. They also have helped us so much with curriculum and content to articulate what we do at Underdog Devs - we are very thankful for it. Being able to do our real time pair programming while combining it with that platform knowledge, adds a lot of value for our students. As an example, they gave us 10 free nano degree seats.
Big Nerd Ranch. A web & mobile app development agency that offers expert training and services - so they basically teach, design and build digital products. I am a big fan because they are super purpose driven and very helpful, always donating stuff like book courses to help us get started. And they also invited me to chat and gave me some ideas for Underdog Devs.
And I would like to give an extra special mention to:
Checkr. Employee background screening solution for companies. Their team has been super supportive with formerly incarcerated people and I’ve seen them do a lot of things, not just talk. Like for instance they actively hire people who have been in prison and give a lot of second opportunities in that sense.
Dropbox. Another cool company supporting our case. They gave us 20 terabytes for free and it’s not just the help but the product itself, highly valuable.
3 investors you like and why?
Sorry because I am going to be impartial again:
John Carmack. He is the legendary programmer creator of the video game Doom and ex CTO at Oculus, and he helped us a lot with support and donations to Underdog Devs.
Alex Marcy. He is the Founder and President at Corso Systems, US based company providing a wide range of software services to businesses. Also a provided a lot of support to our initiative.
Wil Reynolds. Currently a VP of Innovation at Seer Interactive, a big data digital marketing agency. He is one of the coolest people ever and again, super helpful.
What books do you feel everyone should read and why?
A few come to my mind but some I could mention are:
"Deepwork: Rules for Focused Success in a Distracted World” by Cal Newport. Great book to recognize how important it is to focus and learn a bit more about how to improve in that aspect. I found a great deal of value in it.
“Atomic Habits” by James Clear. Well-known and maybe a bit too basic premise, but I really liked how it shares the clear idea that we should be focusing less in setting goals and more in building habits that can actually lead us to these goals.
“A Confederacy of Dunces” by John Kennedy Toole. When you are in a shitty place like I was in prison, sometimes is the simple and funny things what brings some light to the dark. That’s the case with this one.
“The Signal and the Noise: Why so Many Predictions Fail - but Some Don’t” by Nate Silver. Interesting reading about the world of prediction and how to distinguish a true signal from a world full of noisy data.
“How Not to Be Wrong: The Power of Mathematical Thinking” by Jordan Ellenberg. Using the mathematical method to analyze life, the author pulls from key historical developments of this area and ends up exposing some hard-won insights to understand the world in a meaningful way, beyond the sometimes chaotic surface that we experience. It helped me deal with some heavy personal stuff such as the hard time I went through when growing up, and also provided somehow a support to expose some basic fallacies that I was carrying with me.
WILDCARD QUESTION
What is Underdog Devs, why is it important and what advice will you give to underprivileged profiles that want to become software engineers?
Underdog Devs is a non profit community of software engineers who are dedicated to help people from disadvantaged socioeconomic backgrounds get into tech. To do so we help them build a network, acquire skills with high quality pair programming and get hired, while also taking care of their living expenses (housing, food, etc) if they need it and even allocate more resources if for whatever justified reason they need more time to make the transition. For now, we had 3 cohorts, 24 mentees and some cool shout out by top companies like Apple.
Why is it important? Providing life changing help to those with a truly disadvantageous background is why. It is tough for me to see a solution for people who truly come from the bottom and this is what we are trying to build. Because a life changing impact in someone with a middle-upper profile is not the same as someone with a middle-lower one and I see much more focus in the former, even if sometimes is camouflaged as the latter. For instance how are you going to pay a bootcamp and take 3 months off to learn to code, when you are too busy surviving just fighting to get to the next month with whatever job you can get and no support? With our high quality education and guidance for free, pair programming from Monday to Friday every week, paying all the bills and allocating all our resources to our mentees without getting anything back, is how we envision providing this unique help that can improve access for real. It is not about doing this stuff to pick flowers and look good, but to plant them and help them grow out of nothing.
And finally, regarding advice, I want to say 2 main things: skills and network. No bullshit.
Network. Choose 1-2 dev communities and engage. Constantly being around developers in initiatives like technical meetups or volunteering in interesting projects is one of the biggest factors contributing to your success in tech as a software engineer. If a job opens up, you are going to get it because people tend to hire from who they know and it will give more chances than being a random applicant, specially if you come from a disadvantaged background.
Skills. Get your skills ready as soon as possible and ideally in something different that can help you stand out. Get depth. And beyond that specialization angle, I’d recommend focus and consistency as the key ingredients of the not-so-secret sauce. The bootcamps boom maybe has given the image that becoming a software developer / software engineer is easy. It is not. You need a lot of commitment, put in the hours, do what you said you were going to do - be extremely persistent.
One example of this that comes to my mind is with my friend Ryan (with whom I was incarcerated and who eventually got into tech as a mobile dev). Ryan was really into powerlifting and when he was already out of prison, he used to train a lot and compete every weekend while at the same time working in construction and learning to code. I’m very transparent with my mentees and I remember a situation when very clearly I said to him “man, at this pace you are going to need 10 years to make it into tech, you have to sacrifice some powerlifting time”. He did and as I mentioned earlier eventually he made it.
Maybe it sounds like simplistic advice but if you are coming from this type of background, you need to understand that you don’t necessarily have a great signal in your story (at least not as a typical privileged tier 1 profile), so you’ll need to get the skills as soon as possible, work hard, sacrifice, be super persistent and have more courage than others in order to win. And don’t be your worst enemy, don’t get in your own way.
Big thanks Rick for sharing your views with us!
Big thanks to you, reader, for your time and interest!
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