My Journey into Dev Bootcamp

Note 0: I had planned on this being my entire Dev Bootcamp story, but I’m not yet ready to tell the whole thing. I just need some more time. This story covers my journey up to Dev Bootcamp Chicago’s first cohort.

Note 1: If you want to skip all these words and just look at some nice photos, go here.

In 2002, I read Software Craftsmanship on an overnight road trip from Chicago to International Falls, Ontario. Someone had handed it to me at work and I thought it looked interesting. Judging by the cover, it certainly looked different from most of the other software books I’d read.

I read the book with a flashlight in the back seat of my car while a few of us took turns driving. I couldn’t put it down. What I remember most was that it provided me with a vocabulary that I could use to describe myself. As a self-taught software developer, terms like “computer scientist” or “software engineer” never felt right for me. But I could imagine becoming a “software craftsman”. Better yet, the book helped me understand that I was clearly still an “apprentice”.

I clung to that word: apprenticeship. It had a powerful influence on how I viewed my career. The apprenticeship concept was motivating for me because one doesn’t apprentice to simply become a “senior developer”. One apprenticed to become a journeyman, and someday maybe a master craftsman. After reading about what master craftsmen were capable of, I immediately aspired to that role.

A few years later, having re-read Software Craftsmanship multiple times, I was still strongly under the influence of its principles. I was now working at ThoughtWorks, surrounded by an inspiring community of software folks. Thanks to some of those connections and ThoughtWorks’ reputation, I was asked to write a web column about software craftsmanship. I was told that Andy Hunt & Dave Thomas were also writing under the same column! I quickly realized that the only software craftsmanship topic I was actually qualified to write about was apprenticeship, since in my opinion, I hadn’t progressed past that stage yet.

As I focused my writing on apprenticeship, I drew inspiration from the many books and blogs that I’d consumed voraciously during the first four years of my career. Christopher Alexander’s A Pattern Language had completely rocked my world in 2003, and so as I thought about apprenticeship, I naturally started organizing ideas into a pattern language. I started publishing those patterns on my website. Within a few months, I was joined by Adewale Oshineye, my co-author, and discovered by Mary Treseler, our future editor at O’Reilly. That’s right, these ideas evolved from a column, to a loose collection of advice, and four long years later, into a book! We didn’t finish it until 2009 because Ruby on Rails “happened” in 2005. The book could wait, the Rails phenomenon couldn’t.

Skipping ahead to 2011, my friend Corey Haines and I had spent the last few years geeking out on apprenticeship and craftsmanship. I had been running an apprenticeship program at the software consultancy I worked at (Obtiva), and Corey had been touring the country, pair programming with all sorts of awesome people. We started wondering aloud about education, thinking about a better way to create apprentices. Unfortunately, we couldn’t break out of the 2-4 year timeframe.

Then we met Neal Sales-Griffin and Mike McGee (see photo). In April 2011, Neal presented us with an idea for teaching people Rails in just 10 weeks. He believed that with the right structure, people could get jobs or build products in less than three months. It was audacious, and Corey and I were intrigued. Neal and Mike co-founded Code Academy in Chicago that summer, but both Corey and I eventually parted ways with this dynamic duo. Code Academy (eventually called Starter League) wasn’t quite the right fit for us. Their primary mission was to create technical entrepreneurs. Corey and I were more interested in getting people started in technical careers.

In early 2012, while working at Groupon in Chicago, I organized a small summit of coding schools to share ideas and lessons learned. Neal from Code Academy, Jeff Casimir of Hungry Academy (later gSchool, now Turing), and Shereef Bishay from Dev Bootcamp, all participated, along with a few other friends. We met in San Francisco, and Shereef gave us a tour of Dev Bootcamp. I was enthralled by what I witnessed there.

Students spent all of their waking time in the space. Shereef pushed them hard. To help them survive, Shereef had them practice yoga and provided a counselor. The curriculum was still evolving, but it was off to a strong start. Part of their curriculum was actually focused on “engineering empathy”, covering topics such as feedback, authenticity, and systemic oppression. Although it smelled like people needed to shower more often, the atmosphere was incredible.

Here’s a photo I took of Shereef teaching his first cohort. (That’s actually the future CEO of Hack Reactor looking up at him!) I came back later that night, just to hang out with students. I couldn’t get enough.

Shereef and his growing team helped these students through a ground-breaking, intense, 8-week program. The graduates were swiftly employed afterward. That cohort’s vocational success, amplified by this Tech Crunch article, started the world-wide coding bootcamp phenomena.

I went back to work at Groupon, scheming for how I could get involved. Shereef and I kept in touch. By April 2012, he had convinced me to travel periodically to SF to convince employers to start apprenticeship programs. That never panned out. But we kept talking, bouncing ideas off each other. In August, I left Groupon. What I really wanted to do was help companies start apprenticeship programs, I wanted to bridge the technical talent gap. But I couldn’t figure out how to afford that without traveling all the time. I had kids (8, 11, and 13) and wanted to spend the vast majority of my nights at home with them. At that point, I was still involved at Starter League, and was planning to teach a class for them in Chicago. I had also helped get Mobile Makers Academy started in Chicago. But then I went and spent some more time at Dev Bootcamp in San Francisco.

I’d never seen anything like that team. They shared their problems with each other, and listened to each other with an incredible focus. They did yoga together. They cared deeply about their students, and about each other. It was the most authentic workplace I’d ever seen. And Shereef treated me like a peer. He did a great job recruiting me. I was hooked. A few days after that trip, I canceled my Starter League class. (Sorry Neal!)

I got officially involved as a contractor for Dev Bootcamp, helping with curriculum, working from Chicago. As summer moved into autumn, I decided I wanted to come on board full-time. Once I joined, Shereef retroactively gave Jesse Farmer and me our “co-founder” titles due to the influences we’d had on the program in its early days.

But I was still more interested in creating apprenticeships or building software to facilitate learning. I had zero intention of trying to teach, let alone launch anything.

In October, I was there in SF as we welcomed our third and final cohort of the year. During that trip it gradually dawned on me that Chicago really needed a school like this, and that I would need to start it. I had serious reservations about the idea. I’m super-introverted. I had no interest in teaching. I was tired from growing Obtiva and selling it to Groupon. Besides, watching Shereef in action, with his huge personality, glowing with charisma, intimidated the hell out of me. But one of my co-workers assured me that Shereef’s way wasn’t the only way to pull it off. And so I agreed. Dev Bootcamp Chicago was about to happen.

My friend Elliott Garms had already told me that whatever I did next, he wanted to be involved. I felt the same way. As co-founders of Dev Bootcamp Chicago, Elliott and I got to work. I couldn’t even begin to list all of the various tasks required to find and set up that beautiful space of ours in River North, not to mention vetting our awesome first few cohorts. But with the help of the SF team, and some local friends, we got it done.

In the meantime, we had pulled together an incredible team of people to deliver this program: Mike Busch, Jen Myers, Kevin Solorio, Alyssa Diaz, Abi Noda, Nate Delage, and Alex Botsford. Leading this group of people was an absolute privilege. If I ever lead another team even close to that strong, I will be a very lucky & happy person.

Our first cohort, nicknamed the “squirrels”, arrived on April 22nd, 2013.

To be continued… part 2