RoboToaster Presents: Inside the Mind of the “@redsquirrel” Dave Hoover

April 18, 2012

We had a chance to meet Dave at the last TechInMotion - - where he participated as a panelist.

“Make sure to come out to the next TechInMotion which will be held May 10th at the 1871 location at the Merchandise Mart. Event gets kicked off 6:00 PM. Check out the Meetup page for more details!”

The more we spoke, the more interesting we found his story and had to put out an interview to share it!

Dave, hope all is well and thanks for taking the time to sit down for a little Q and A! What you have been doing for Chicago and the technology community has been great and I’m sure everyone is anticipating hearing a little more about your story.

Q) First off, I have to ask. RedSquirrel, what’s the background story?

A) I’m usually a pretty low-key guy, tending on the quieter side. Sometimes, though, I become very… um, shall we say, “active”.When I go into active-mode, I like to climb on things like trees and buildings. Because of this, my college buddies’ nickname for me was “squirrel”.

Then, about 12 years ago, my brother and I were starting a little web design company as a side business. Since we’re both redheads, we came up with as our domain name. We’ve both moved on with our careers, but I kept the name, and the domain. I still have dreams of working with him again someday and reinventing what RedSquirrel means.

Plus, it’s fun to have a nickname like RedSquirrel. I’d hate to have a boring nickname, like my initials…

Q) You are a busy man, with a family in the suburbs, being a Sr. Manager of Software Engineering @ Groupon, a mentor to startups, an advisor at CodeAcademy and who knows what else. How do you keep it all together?

A) I’ve been married to an amazing woman for nearly 15 years. Her patience, strength, friendship, humor, and intelligence are the glue that keeps my life “together”. Our marriage counselor is pretty great too.


At Groupon I “manage” a couple teams. I don’t actually manage them, though, since both of them have strong leadership already. So I just do some coding, some system architecture, handle issues, recruit new people, get stuff out of their way, and do other “make life better for software developers” activities like instigating happy hours, leading our dodgeball team, and creating a developer lounge. Having great teams frees me up from needing to work crazy hours at Groupon, so I work very hard to ensure I always have great teams.

I also mentor and advise some other startups in Chicago. Ever since I’ve been a software developer, I’ve always had extracurricular activities going on. I couldn’t imagine not being involved with other people and companies outside my “normal” job. Plus, these activities have invariably paid off for my employers.

I make the schedule work by using my breakfasts and lunches for extracurricular conversations, and limit myself to spending no more than one dinner a week away from my wife and kids. I’d much rather wake up early for a breakfast meeting with you than miss dinner with my family for a beer with you after work.

One of the secrets to pulling this off is having my own mentor who I meet with every month or so. His name is Jerry Folz and his insights are a huge help in keeping my life in balance.

Q) Reading through your blog you can definitely tell you’re a family man, how have they played a role in your career development?

A) I married Staci when I was 23, and my daughter was born when I was 24. Because of this, I’ve never had to make a big transition from being single or childless to being a family man. I’ve seen a lot of other people make that transition and then completely fall off the radar after having kids. I suppose it’s difficult to regain your balance. I’ve pretty much always been a family man. This was sometimes tough in my 20’s, but overall it has been an advantage. Left to my own devices, I’d be an obsessive workaholic, so the constraints I have from being a family man help keep me healthy. My family motivates me to not work long hours, they keep me physically active since they all play sports, and the lessons I’ve learned from being married for 15 years and helping raise 3 kids to this point give me a helpful perspective on challenging situations in the workplace. I guess my training and experience as a child and family therapist doesn’t hurt either.

Q) I heard through the grapevine you love riding the Metra? Does living out in Wheaton help you decompress the day/get ready for the day?

A) I do love riding the Metra. I’ve been taking it since 2001. I’ve turned that time into a very productive commute over the years. It’s a perfect time to read books about software development and work on side projects. If I had to point to any specific place where my “software engineering education” happened, I would point to the wonderful, library-like, Union Pacific West Line.

And yes, it’s a great decompression time between a busy household and busy startups.

Q) It seems like you took a pretty unique path to where you are today in the software engineering field. Were you always doing programming when getting both your B.A. and Master’s or is it something that came up out of the blue?

A) I’ve always been interested in programming. I played with Logo when I was in grade school and BASIC when I was in middle school, but I was never able to keep my momentum, so I gave up. I didn’t pick it up again until I was 25, and I finally got over the hump when I was 26. I was infected with the dot-com mania of 1999 when I was living in Seattle, and that set me down the path of learning how to be a web developer. At the time, it felt very out of the blue, but looking back, I can see the foreshadows.

Q) We will change gears a bit now. I can’t help but notice the negativity DHH “David Heinemeier Hansson” spits out on Twitter about Groupon’s recent IPO. Being a big player at Groupon yourself, an avid Ruby on Rails user and implementer, is it hard to support the framework when the creator is so negative about a company that built their platform with it?

A) I will always be grateful to David for creating Rails. I learned Ruby in 2002, after spending my first couple year programming in Perl and Java. Ruby felt like an excellent blend of the two languages. Yet, it wasn’t until Rails hit the scene that I was able to get paid to write Ruby code. Rails was just what the doctor ordered when I started using it in 2005. It brought me back to web development after a couple years of growing disenchanted with the web while I was at ThoughtWorks.

David rubs me the wrong way sometimes, but I usually agree with him on technical and business topics. I’ve ignored his thoughts about Groupon. But I ignore most outsiders’ thoughts about Groupon.

Q) What was your take on the article on the Midwest Mentality? Are we all taking the safe route?

A) I thought it was cool that someone would take some time to research and report about Chicago’s tech scene. He did get some things right. I suppose I’m a good example of his point about getting married early and not working 24/7 for my employers. My blog post about Eating Million Dollar Cakes is an example of the Midwest Mentality. 37signals is probably the best example. I think we generally prefer millions over billions, because it means we get to have a great quality of life. My hope for the Chicago startup scene is that we can have a healthy mixture of big wins and awesome, quickly-profitable companies. I believe we’ll achieve that healthy mix within the next 5 years.

The funny thing about that article, though, is that Groupon spoils his whole premise. It was bizarre to read about the critical importance of “hockey-stick companies” that “propel an ecosystem forward” and then have him ignore the fact that this is exactly what has happened. He avoided having to explain Groupon in that article by saying he’d cover it in a future article. (Still waiting on that future article.)

Q) To branch off that, there are so many startups popping up in Chicago. Is that because the influx of funding that has hit the city or is more development talent being present? Maybe both?

A) At its root, it’s mostly because of the influx of capital. The development talent has been here forever, mostly caught up in the trading firms and hedge funds. The existence of capital for startups has enticed some of our previously under-the-radar development talent to take the red pill. Which is awesome.

There have also been plenty of developers relocating to Chicago from all over the place. On my teams at Obtiva and Groupon, I’ve hired people from Ohio, Michigan, Indiana, Iowa, but also from San Francisco, and even some people from Australia.

Q) There is always tons of talk about the impact Silicon Valley has on the technology industry. I imagine you have interacted with plenty of the professionals in that arena. In your opinion, what can Chicago do to continue the advancement of the community and start to compete at a higher level than in the previous years?

A) I think we need to keep doing what we’ve been doing. We need to keep being ourselves. Let’s not try to be Silicon Valley. I don’t want to live and work in Silicon Valley. I want to work in Chicago and do it our way. Silicon Valley is an amazing place. The ratio of tech people to non-tech people is unbelievably high. When I ride the Caltrain, I’m as likely to see JavaScript code on someone’s laptop as I am a Powerpoint deck. That’s cool, and has a great generative effect on that community. That’s not going to happen in Chicago. And that’s fine. The thing I don’t see in Silicon Valley is the contagious enthusiasm of our growing community. This is Chicago’s most unique asset right now. If we can keep our momentum through growing our businesses, creating profitable startups, and achieve some big exits and IPOs, then the combination of our community and local capital will create something extraordinary in the coming decades.

Q) Code Academy has generated a lot of traction in the Chicago community and has been generating really positive response, what was it like to a part of everything during its infancy?

A) In early spring of 2011, my friend and fellow software developer Corey Haines introduced me to Neal Sales-Griffin. Neal had a beautiful slide deck and a compelling vision for Code Academy. I was immediately excited about Code Academy because I was actively looking for new sources of apprentice candidates for Obtiva’s apprenticeship program. (Now Groupon’s apprenticeship program.) When Neal heard about my book and my background as a self-taught software developer, he got excited too. As I got to know Neal and his co-founder Mike McGee, I was increasingly impressed with their talents, work ethic, networking abilities, and commitment to learning. In short, I became infected with the Code Academy virus.

I had stepped into an advisory role, so I went with them to talk to a VC firm. That was certainly enlightening. They didn’t end up needing VC money, though. So I offered to invest some angel-level money. Turned out they didn’t even need that. They’ve been able to completely bootstrap the company and have been profitable from the start. I did end up with some equity due to my participation as an advisor and my help with the mentoring program.

A year later, they’re seriously killing it. They’ve been the tip of the spear for 1871. Neal is stealing the spotlight on the news. They’re growing steadily, and they’re hustling more than ever.

Q) Your book, Apprenticeship Patterns, what was the inspiration behind that?

A) I was inspired by the book “Software Craftsmanship: The New Imperative” when I read it in 2002. Being self-taught, I felt a little lost when it came to computer science and software engineering. This book gave me a framework to help me see where I stood. I wasn’t a master, I wasn’t yet a journeyman. I was an apprentice! This realization changed my career.

I started blogging and thinking a lot about software craftsmanship. While I was working at ThoughtWorks in 2005, I was asked to write a column for on that topic. At the time, I still considered myself an apprentice, so it seemed natural to write a column about apprenticeship. Soon after that, I realized that there was a missing book in the software development literature. There weren’t yet any good books about how to go from apprentice to journeyman. You can read the rest of the story on my blog.

Q) What’s next for Dave Hoover?

A) I have some work to do at Groupon that I’m really excited about. I want our engineering department to be a better role model to Chicago and the world when it comes to a strong culture of innovation, community participation, open source contributions, and thought leadership. My teams there are working on some capabilities that are integral to Groupon’s success, and I’m excited about seeing that come to fruition in the coming year.

At the same time, I’ve dipped a toe into the world of angel investing. I’m an investor and advisor at StyleSeek, an awesome Chicago startup that’s basically a mixture of Tumblr and Pandora for men’s apparel. My history with them is similar to my history with Code Academy: I was introduced to the founder/CEO and quickly realized he was someone that I should have my interests aligned with. Just as I am with Neal and Code Academy, I’m confident that Tyler Spalding, the founder/CEO of StyleSeek, is growing something remarkable.

Finally, I remain convinced that apprenticeship can be an excellent alternative and supplement to higher education. I’m working with Dale Stephens of UnCollege to form a broader and richer community around apprenticeship. I think this is particularly important in a time when there are so many people (particularly young people) looking for work who need just a little help to get over the hump in order learn the skills needed to land the right job. Not to mention the employers who struggle to find “qualified” candidates. Those employers who can adapt to take on enthusiastic apprentices will soon after find themselves with a strong culture and a solid workforce. Go sign up at to hear about what’s coming next.

Thanks a ton Dave. We really enjoyed hearing your responses!


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